Simple exploration of 5750-76-5

Statistics shows that 5750-76-5 is playing an increasingly important role. we look forward to future research findings about 2,4,5-Trichloropyrimidine.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.4231, as common compound, the synthetic route is as follows.5750-76-5

2,4,5-Trichloropyrimidine (250 mg, 1.36 mmol) and ferric acetylacetonate (24 mg, 0.07 mniol) were taken up in tetrahydroruran (2.7 ml) and the reaction was cooled to -78 C.Methylmagnesium bromide (0.45 ml of 3 M in THF, 1.36 mmol) was added dropwise and the mixture was stirred at -78 C for one hour. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by Combiflash (0-10% diethylether in hexanes) to provide 2,5- dichloro-4-methylpyrimidine (99 mg, 0.61 mmol, 45 %) as a white solid. MS APCI: [M+H]+ m/z 163.0.

Statistics shows that 5750-76-5 is playing an increasingly important role. we look forward to future research findings about 2,4,5-Trichloropyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ALTMAN, Michael, D.; ARRINGTON, Kenneth, L.; BURCH, Jason; COTE, Bernard; FOURNIER, Jean-Francois; GAUTHIER, Jacques, Yves; KATTAR, Solomon; KNOWLES, Sandra Lee; LIM, Jongwon; MACHACEK, Michelle, R.; NORTHRUP, Alan, B.; REUTERSHAN, Michael, H.; ROBICHAUD, Joel, S.; SCHELL, Adam, J.; SPENCER, Kerrie, B.; WO2011/75560; (2011); A1;,
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The origin of a common compound about 213265-83-9

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

213265-83-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

0.07 G OF sodium hydride (60% OIL SUSPENTION) was suspended in 3 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution of 0.14 g of 2-ethylpiperidine was added dropwise at room temperature therein slowly, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 1 ml of tetrahydrofuran solution of 0.2 g of 4,6-dichloro- 5-FLUOROPYRIMIDINE at room temperature, and stirred for 4 hours. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.22 g of 4-chloro- 6- (2-ETHYLPIPERIDINO)-5-FLUOROPYRIMIDINE. 1H-NMR : 0.89 (t, 3H), 1.50-1. 76 (m, 7H), 1. 78-1. 91 (m, 1H), 3.08 (td, 1H), 4.35-4. 42 (m, 1H), 4.54-4. 62 (m, 1H), 8.10 (s, 1H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2004/99160; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The origin of a common compound about 155-12-4

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 155-12-4, 2-Chloro-5-fluoropyrimidin-4-one, other downstream synthetic routes, hurry up and to see.

155-12-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 155-12-4, name is 2-Chloro-5-fluoropyrimidin-4-one, molecular formula is C4H2ClFN2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-chloro-5-fluoro-3H-pyrimidin-4-one was stirred in DME/DMF under nitrogen at 0 C. Sodium hydride was added in portions. After 10 min, lithium bromide was added and the reaction stirred for 15 min at r.t. alpha-Bromo-o-tolunitrile was added, and the reaction stirred at 65 C. for 8 h. The solution was diluted with EtOAc, washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography gave the title compound. 1H NMR (400 MHz, CDCl3): delta 7.81 (s, 1H), 7.74 (dd, 1H, J=7.6, 1.2 Hz), 7.59 (td, 1H, J=7.6, 1.2 Hz), 7.45 (t, 1H, J=7.6 Hz), 7.15 (d, 1H, J=7.6 Hz), 5.67 (s, 2H). MS (ES) [m+H] calc’d for C12H7N3OFCl, 264, 266; found 264, 266.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 155-12-4, 2-Chloro-5-fluoropyrimidin-4-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Christopher, Ronald J.; Covington, Paul; US2007/60529; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
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The origin of a common compound about 1780-26-3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1780-26-3, its application will become more common.

1780-26-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1780-26-3 as follows.

To a slurry of 4,6-dichloro-2-methylpyrirnidine (1-1) (5.00 g, 30.67 mmol, 1.0 eq.) and cesium carbonate (15.0 g, 46.05 mmol, 1.5 eq.) in DMF (250 mL) at 0 C under nitrogen was added a solution of 3,5-dimethyl-lH-l,2,4-triazole (2.98 g, 30.67 mmol, 1.0 eq.) in DMF (50 mL) via a dropping funnel over 1 hour. The reaction was then warmed to room temperature and stirred for 1 hour. The reaction was quenched by addition of water (500 mL) and extracted with ethyl acetate (3 x 400 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The crude product was purified by silica gel column chromatography (0-30% ethyl acetate in hexanes) to afford 4-chloro-6-(3,5-dimethyl-lH-l,2,4-triazol-l-yl)-2-methylpyrimidine (1-2) as a white solid. ‘Eta NMR (300 MHz, CDC13) delta 7.75 (s, 1H), 2.91 (s, 3H), 2.72 (s, 3H), 2.41 (s, 3H). LRMS mlz (M+Ff) 224 found, 224 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1780-26-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; DUDKIN, Vadim, Y.; KIM, June, J.; KUDUK, Scott, D.; MCVEAN, Carol; REGER, Thomas; STEEN, Justin; STEELE, Thomas; WO2013/52526; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Simple exploration of 1500-85-2

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1500-85-2 as follows., 1500-85-2

4-Amino-7H-pyrrolo [2,3-d] pyrimidine (0.60 g, 4.47 mmol) was weighedN-iodosuccinimide (1.51 g, 6.71 mmol)Dissolved in 100 ml of acetonitrile,And heated at 120 for 24h.After the reaction is completed, the solvent is evaporated,With dichloromethane mixed with water extraction,The organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure.The residue was purified by column chromatography to give 0.96 g of a yellow solid (82.51% yield).

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sichuan University Huaxi Hospital; He Yang; Chai Yingying; Chen Bojiang; Zhou Xinglong; Li Changfu; Qiu Zhixin; Li Weimin; (11 pag.)CN106831790; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Sources of common compounds: 36315-01-2

The chemical industry reduces the impact on the environment during synthesis 36315-01-2, I believe this compound will play a more active role in future production and life.

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 36315-01-2 as follows., 36315-01-2

EXAMPLE 1 N-(2-Chloroimidazo[1,2-a]pyridine-3-ylsulfonyl)-N’-(4,6-dimethoxy-2-pyrimidinyl)urea (Compound No. 1) STR55 In 30 ml of acetonitrile are dissolved 2.32 g (0.01 mole) of 2-chloroimidazo[1,2-a]pyridine-3-sulfonamide and 2.02 g (0.02 mole) of triethylamine, followed by addition of 1.60 g (0.01 mole) of phenyl chloroformate with stirring at 10 to 20 C. The mixture is further stirred at 20 to 25 C. for 30 minutes, and to the mixture are added 1.00 g (0.010 mole) of methanesulfonic acid and then 1.55 g (0.01 mole) of 2-amino-4,6-dimethoxypyrimidine. The mixture is stirred at 60 C. for 15 minutes. After cooling, the crystals which separates out are collected by filtration and washed with water 3 times with 10 ml of water each. The crystals were then dried in vacuo over P2 O5 to give 3.42 g (yield 83.0%) of the title compound. m.p. 183-184 C. (decomp.). NMR (DMSO-d6) delta: 3.95 (s, 6H), 6.0 (s, 1H), 7.3-7.5 (m, 1H), 7.5-7.9 (m, 2H), 8.97 (d, 1H), 10.65 (s, 1H), 12.8 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 36315-01-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4994571; (1991); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Brief introduction of 1820-81-1

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1820-81-1, 5-Chlorouracil, other downstream synthetic routes, hurry up and to see.

1820-81-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 1; compound 1 A 50OmL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 1100C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).; Example 3; compound 78NMM, THF -780CA 500-mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).; Example 4 compound 80A 500-mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).; Example 5 compound 84a bA 50OmL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 1100C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1820-81-1, 5-Chlorouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; WO2008/79719; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Extended knowledge of 90213-66-4

Statistics shows that 90213-66-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

90213-66-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below.

A stirred solution of S-1 (2.00 g, 10.7 mmol) in CH2Cl2(20 mL) taken in a round- bottom flask was charged with DIPEA (3.7 mL, 21.4 mmol), DMAP (0.039 g, 0.32 mmol) and p-toluene sulfonyl chloride (2.25 g, 11.7 mmol) successively at ambient temperature under nitrogen atmosphere. The reaction mixture was stirred for 2 h at same temperature. The reaction mixture was diluted with CH2Cl2(100 mL) and was washed with water (40 mL) and HCl (1 N, 40 mL). The combined organic layer was washed with brine (1 ¡Á 50 mL), dried over anhydrous Na2SO4and was concentrated under reduced pressure. The obtained residue was washed with hexanes (2 ¡Á 50 mL) and was dried under vacuum to afford S-2 (3.50 g, 95%, AMRI lot IN-SKY-C-03) as an off-white solid. The compound was characterized by1H NMR analysis.1H NMR (400 MHz, CDCl3): delta 8.03 (d, J = 8.4 Hz, 2H), 7.68 (d, J = 4 Hz, 1H), 7.29 (d, J = 8.12 Hz, 2H), 6.60 (d, J = 4 Hz, 1H), 2.36 (s, 3H).

Statistics shows that 90213-66-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; SOUTHERN RESEARCH INSTITUTE; AUGELLI-SZAFRAN, Corinne, E.; SUTO, Mark; GALEMMO, Robert; MOUKHA-CHAFIQ, Omar; GUPTA, Vandana; ANANTHAN, Subramaniam; (254 pag.)WO2017/106771; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
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A new synthetic route of 4595-59-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 4595-59-9, 5-Bromopyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 4595-59-9, blongs to pyrimidines compound. 4595-59-9

Argon is bubbled for 15 minutes into a mixture of 9.3 g of tert-butyl 1-piperazinecarboxylate, 7.95 g of 5-bromopyrimidine and 6.5 g of sodium tert-butoxide in 250 ml of toluene, which is then heated at reflux, 0.277 g of palladium acetate and 1.7 ml of tri-tert-butylphosphine are added and reflux is continued for 24 hours. 0.277 g of palladium acetate is added and the mixture is heated at reflux for 8 hours. The reaction mixture is cooled to AT, water is added, the mixture is subjected to extraction with AcOEt, the organic phase is filtered and dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with DCM, then with a DCM/AcOEt (50/50; v/v) mixture and finally with a DCM/MeOH (95/5; v/v) mixture. This gives 3.95 g of the expected product following recrystallization from a DCM/hexane/iso ether mixture.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Patent; sanofi-aventis; US2005/176722; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A new synthetic route of 7752-82-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below., 7752-82-1

To a solution of 2-amino pyridine (30 g, 0.31 mol) in DME (120 mL) was added chloro acetone (40.5 mL, 0.47 mol) at room temperature. The reaction mixture was heated to reflux, and then stirred for 48 hours. The volatiles were concentrated under reduced pressure. Then the residue was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-2 (20 g, 48%) as a liquid. Mass (m/z): 133 [M++1]. 1H NMR (200 MHz, dmso-d6): delta8.05 (d, J=8.2 Hz, 1H), 7.35 (s, 1H), 7.1 (t, J=6.8 Hz, 1H), 6.7 (t, J=6.8 Hz, 1H), 6.5 (d, J=8.2 Hz, 1H), 2.45 (s, 3H). To a solution of Int-2 (10 g, 76.7 mmol) in acetonitrile (50 mL) was added N-iodo succinamide (20.4 g, 80 mmol) portion wise at room temperature and then stirred for 48 hours. The precipitated solid was filtered off. The crude material was re-crystallized from ethyl acetate/water to afford Int-3 (9 g, 49%) as solid. Mass (m/z): 259 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.22 (d, J=8 Hz, 1H), 7.47 (d, J=7.2 Hz, 1H), 7.29 (t, J=7.0 Hz, 1H), 2.35 (s, 3H). To a solution of Int-3 (6.0 g, 29.2 mmol) in IPA-H2O (75 mL, 2:1) was added PdCl2(dppf).DCM (4.7 g, 5.8 mmol), followed by the addition of tert-butyl amine (3.1 g, 43.8 mmol) at room temperature and the resulting reaction mixture was degassed for 15 minutes. Then Int-4 (2.9 g, 18.6 mmol) was added to the reaction mixture at room temperature. The reaction mixture was heated to 100 C. and then stirred for 16 hours. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (3¡Á100 mL), washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-5 (1.6 g, 28%). Mass (m/z): 244 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (t, J=5 Hz, 2H), 7.71 (s, 1H), 7.63-7.55 (m, 2H), 7.34 (t, J=7 Hz, 1H), 6.94 (t, J=7 Hz, 1H), 2.43 (s, 3H). To a stirred mixture of 5-bromo 2-aminopyrimidine (8 g, 45.97 mmol) in MeOH-CH3CN (200 mL) in a steel bomb were added Pd(CH3CN)2Cl (2.38 g, 9.19 mmol), racemic-BINAP (5.7 g, 9.19 mmol), DIPEA (10.4 mL, 53.7 mmol) at room temperature and then closed the steel vessel tightly. Then CO gas (100 psi) was purged into the steel bomb and the stirring was continued at 120 C. for 45 hours. The reaction mixture was allowed to room temperature. The reaction mixture was filtered through a pad of celite. The celite pad was washed with excess of methanol and the filtrate was concentrated under vacuum. The crude material was purified by column chromatography eluting with 0.75% MeOH/DCM to afford Int-6 (5 g, 71%) as solid. Mass (m/z): 154 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.65 (s, 3H), 7.49 (brs, 2H), 3.58 (s, 3H) To a stirred mixture of Int-5 (3 g, 2.34 mmol) and Int-6 (1.8 g, 12.34 mmol) in 1,4-dioxane (90 mL) were added Pd(OAc)2 (279 mg, 1.23 mmol) and Xanthpos (710 mg, 1.23 mmol) followed by cesium carbonate (6 g, 18.5 mmol) at room temperature. The resulting mixture was degassed and stirred at reflux temperature for 30 hours. The reaction mixture was cooled to room temperature and then stirred for 15 minutes. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum. The crude material was purified by column chromatography eluting with 1.5% MeOH/DCM to afford Int-7 (0.6 g, 13.6%) as solid. Mass (m/z): 361.2 [M++1]. 1H NMR (500 MHz, dmso-d6): delta 10.76 (brs, 1H), 8.97 (s, 2H), 8.56 (d, J=7, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.5 Hz 1H), 7.34-7.29 (m, 2H), 6.99 (t, J=76 Hz, 1H), 3.84 (s, 3H), 2.46 (s, 3H). To a stirred solution of Int-7 (0.5 g, 1.38 mmol) in MeOH-CH3CN (1:2, 25 mL) was added aqueous NH2OH solution (15 mL) at 0 C. After being stirred for 20 minutes at the same temperature, NaOH (0.44 g, 11.10 mmol) in water (1 mL) was added drop wise to the reaction mixture at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 days. The volatiles were concentrated under vacuum and the obtained residue was diluted with water and neutralized to about pH 7 with 2 N HCl at 0 C. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum to afford the title compound (0.4 g, 80%) as off-white solid. Mass (m/z): 362.1 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 11.2 (bs, 1H), 10.5 (s, 1H), 9.12 (bs, 1H), 8.84 (s, 2H), 8.57 (d, J=7.0 Hz, 1H), 8.45 (d, J=5.0 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 7.25 (d, J=4.0 Hz, 1H), 6.98 (d, J=7.0 Hz, 1H), 2.49 (s, 3H). 13C NMR (125 MHz, dmso-d6): delta 160.7, 157.1, 153.0, 148.7, 144.5, 142.3, 137.9, 125.2, 123.9, 118.8, 118.2, 117.0, 116.6, 112.7, 112.4, 14.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/29638; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia