Pyrimidines

Synthetic Route of 74901-69-2, 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.74901-69-2, name is 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, molecular formula is C6H4Cl2N2S, molecular weight is 207.08, as common compound, the synthetic route is as follows.

25.1 2-[1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-propan-2-ol (III-8) 2.7 g (II) are placed in 30 ml dioxane, then 6.8 ml diisopropyl-ethylamine and 1.8 g 2-(1-aminocyclopropyl)-propan-2-ol (see Liebigs Ann. Chem. 1978, 1194) are added. The reaction mixture is heated to 160 C. until there is no further reaction, and after cooling it is evaporated to dryness. The residue is combined with ice water. The product is extracted with dichloromethane and purified by chromatography. 125 mg (III-8) are obtained as a solid. Analytical HPLC-MS (method A): RT=1.08 min.

Statistics shows that 74901-69-2 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; Nickolaus, Peter; US2013/225609; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1119280-66-8, 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 1119280-66-8 as follows.

step 1 : To a stirred mixture of sodium hydride (12.5 g, 520 mmol, 60% in mineral oil) in anhydrous THF (300 mL) at 0 C was added dropwise 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (40.0 g, 262 mmol) dissolved in anhydrous THF (200 mL). The reaction mixture was stirred at 0 C for 15 min them SEMCl (52.5 g, 315 mmol) was added dropwise. The mixture was then stirred at RT for 1 h and then diluted with EtOAc. The organic layer was washed with water and brine, dried(Na2S04), filtered and concentrated under reduced pressure. The crude product was purified by Si02 chromatography to afford 42 g (56.4%o) of 2-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-i ]pyrimidine as an orange oil. A high-pressure tube charged with 2-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2- i ]pyrimidine (2.23 g, 7.90 mmol), tributyl(l-ethoxyvinyl)stannane (3.7 g, 10.27 mmol), and Pd(PPh3)2Cl2 (200 mg) in degassed DMF (20 mL) under N2 was sealed and heated at 100 C for 16 h. The reaction mixture was cooled, diluted with EtOAc, and filtered through a pad of Celite to remove Pd solid. The filtrate was washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The crude product was dissolved in anhydrous THF (0.3 M), and 2N HC1 (5.0 eq.) was added. The reaction mixture was stirred at RT under N2 for 16 h, poured into 10% aq. NaOH solution, and then extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The crude product was purified by Si02 chromatography to afford 1.5 g (66%) of l-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanone as pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.09 (s, 1H), 7.66 (d, J = 3.2 Hz, 1H), 6.89 (d, J = 4.8 Hz, 1H), 5.60 (s, 2H), 3.49 (t, J = 8.0 Hz, 2H), 2.88 (s, 3H), 0.901 (t, J = 8.0 Hz, 2H), -0.053 (s, 9H); MS(ESI) m/z: 291 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1119280-66-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James John; MATHIEU, Simon; RUDOLPH, Joachim; LEE, Wendy; WO2013/92940; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 799842-07-2 ,Some common heterocyclic compound, 799842-07-2, molecular formula is C16H19BrFN3O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 1 Preparation of Compound I A 2 L four-necked flask charged with 61 g of di(p-tolyl) phosphinate (compound (VII), prepared by referring to Org. Lett. 2005, 7, 4277?4280) and 1 L of tetrahydrofuran solution was cooled down to -20 C., followed by adding dropwise 109 mL of butyllithium solution (2.5 M) at the same temperature. After the addition is completed, the mixture was stirred for 30 minutes. A solution comprising N-(5-(bromomethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methyl methanesulfonamide (compound V) was then added dropwise while keeping the temperature at -20 C. After the addition is completed, the reaction was continued until the starting materials were completely consumed. The reaction was quenched with 1 L of water. The liquid was separated. The aqueous phase was extracted with 0.5 L of ethyl acetate. The organic phase was combined, and concentrated. The resultant solid was recrystallized in toluene to give compound I with a yield of 87%, and HPLC purity of >99%. (0045) 1H NMR (400 MHz, CDCl3) delta: 1.24 (6H, d, J=6.4 Hz), 2.38 (6H, s), 3.423.51 (7H, m), 3.87 (2H, d), 6.896.93 (2H, m), 7.107.16 (6H, m), 7.287.32 (4H, m).

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. 799842-07-2, N-[5-Bromomethyl-4-(4-fluorophenyl)-6-isopropylpyrimidine-2-yl]-N-methylmethane sulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Asymchem Laboratories (Tianjin) Co., Ltd.; Asymchem Life Science (Tianjin) Co., Ltd.; Tianjin Asymchem Pharmaceutical Co., Ltd.; Asymchem Laboratories (Fuxin) Co., Ltd.; Jilin Asymchem Laboratories Co., Ltd.; HONG, Hao; GAGE, James; LI, Jiuyuan; SHEN, Litao; ZHANG, Lei; DONG, Changming; (12 pag.)US2017/22169; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 74901-69-2, name is 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, molecular formula is C6H4Cl2N2S, 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. Computed Properties of C6H4Cl2N2S

6. SYNTHESIS OF [2-(5-BENZOXAZOL-2-YL-2,5-DIAZABICYCLO[2,2,1]HEPT-2-YL)-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YL]-(TETRAHYDROPYRAN-4-YL)-AMINEExample 296.1 (2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)-(tetrahydropyran-4-yl)-amine (III-5)0.68 g (II) are placed in 6 ml dioxane, then 1.72 ml diisopropylethylamine followed by 0.6 g 4-aminotetrahydropyran are added. The reaction mixture is heated at 130 C. until there is no further reaction and after cooling evaporated down. The product is treated with water in the ultrasound bath, suction filtered and dried. 0.66 g (III-5) are obtained as a solid.Analytical HPLC-MS (method A): RT=1.08 min.

With the rapid development of chemical substances, we look forward to future research findings about 74901-69-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/46096; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3177-20-6, Adding some certain compound to certain chemical reactions, such as: 3177-20-6, name is Methyl 2,4-dichloropyrimidine-5-carboxylate,molecular formula is C6H4Cl2N2O2, 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 3177-20-6.

Methyl 2-chloTo-4-{i2-(2-hYdroxyethoxy)ethyl amino}pyrimidine-5-carboxylate (1254) (1255) A solution of methyl 2,4-dichloropyrimidine-5-carboxylate (252 mg, 1.22 mmol) in i- PrOH (6 mL) was added 2-(2-aminoethoxy)ethanol (122 iL, 1.22 mmol) and DIEA (319 mu,, 1.83 mmol) at 0 °C. After 1.5 h the volatiles were removed under a reduced pressure and the residue was purified by ISCO silica gel column to provide the title compound (243 mg, 72 percent) as a white solid. 1H N R (400 MHz, CDCI3) delta 8.67 (s, 1H), 3.90 (s, 3H), 3.82-3.74 (m, 4H), 3.70 (t, J = 5.2 Hz, 2H), 3.67-3.61 (m, 2H), 2.17 (t, J = 6.3 Hz, 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. 3177-20-6, Methyl 2,4-dichloropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; FRYE, Stephen; WO2015/157127; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1193-21-1, 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. 1193-21-1, name is 4,6-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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.

(9) Synthesis of intermediate (c’) 298 mL of methanol is added to 387 mL (7.98 mol) of hydrazine monohydrate, followed by cooling to 10C (internal temperature). To the resulting mixture is gradually added 149 g (1.00 mol) of 4,6-dichloropyrimidine (at an internal temperature of 20C or lower), and then the ice bath is removed to allow the internal temperature to increase to room temperature, followed by stirring the mixture for 30 minutes at the same temperature. Thereafter, the mixture is further heated to an internal temperature of 60C, and stirred for 5 hours at the same temperature. After completion of the reaction, 750 mL of water is added thereto, and the reaction solution is cooled with ice to an internal temperature of 8C. Crystals precipitated are collected by filtration, spray washed with water and with isopropanol, and dried for 36 hours at room temperature to obtain 119 g (white powder; yield: 84.5%) of the intermediate (c’). Results of NMR measurement of the thus-obtained intermediate (c’) are as follows. 1H-NMR (300 MHz, d-DMSO): 7.80 (s, 1H), 7.52 (s, 2H), 5.98 (s, 1H), 4.13 (s, 4H)

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1193-21-1, 4,6-Dichloropyrimidine.

Reference:
Patent; FUJIFILM Corporation; EP2474576; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1445-39-2, 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. 1445-39-2, name is 2-Amino-5-iodopyrimidine. A new synthetic method of this compound is introduced below.

Triethylamine (1.0 mL) was added to a degassed solution of 2-amino-5-iodopyrimidine (275 mg), tert-butyl 3-ethynylphenyl (methyl) carbamate (Intermediate 42) (298 mg) PdCl2 (PPh3) 2 (17 mg) and cuprous iodide (1.25 mg) in DMF (5.0 mL). The mixture was heated to 60C for 4 hours and concentrated in vacuo. Purification by flash chromatography on silica using 0- 10% MeOH in DCM as eluent gave the title compound as a yellow solid (344 mg, 86%). lH NMR (CDCl3) 1.47 (s, 9H), 3.27 (s, 1H), 5.22 (s, br, 2H), 7.23-7. 31 (m, 3H), 7. 39 (s, 1H), 8.45 (s, 2H); MS m/e MH+ 325.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1445-39-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/60970; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, molecular weight is 144.1518, as common compound, the synthetic route is as follows.Quality Control of 4,6-Dihydroxy-2-mercaptopyrimidine

General procedure: A mixture of an aldehyde (0.25 mmol), 2-thiobarbituric acid (0.5 mmol), ammonium acetate (0.3 mmol), and CuFe2O4 (10 mol%), with distilled H2O, in an open tall beaker was irradiated inside microwave oven at 100 W for an appropriate time (monitored by TLC). After completion of the reaction, for removing the catalyst, the hot solution was filtrated with external magnetic for several times. The solvent was evaporated, and the precipitate was washed from ethanol and hot water to afford the pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Naeimi, Hossein; Didar, Asieh; Rashid, Zahra; Journal of the Iranian Chemical Society; vol. 14; 2; (2017); p. 377 – 385;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 147118-40-9 ,Some common heterocyclic compound, 147118-40-9, molecular formula is C23H30FN3O6S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 12(E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5- yl](3i?,55)-3,5-dihydroxyhept-6-enoic acid, hemi-calcium salt I; Tetrahydrofuran (35 ml) is added to weighed methyl ester II (6 g). 40percent solution of LiOH (10 ml) is added to the solution over 5 minutes, and the heterogenous mixture is stirred vigorously for 3 hours and then poured into a separatory funnel containing demineralized water (150 ml) and hexane (50 ml). After complete separation, ethyl acetate (40 ml) is poured into the aqueous phase and calcium acetate (2 g) is added. After 10 minutes of vigorous stirring, the phases are separated, and the aqueous phase is reextracted with ethyl acetate (20 ml). The ethyl acetate extract is washed with demineralized water (2 x 5 ml), dried, and evaporated, and the evaporation residue is dissolved in acetone and sprayed into the stream of an inert gas. 4.5 g (74 percent) of amorphous rosuvastatin is obtained. HPLC: 99.1 percent.

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. 147118-40-9, Rosuvastatin methyl ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZENTIVA, a.s.; WO2007/121; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 6299-87-2, 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. 6299-87-2, name is 6-Hydroxypyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below.

Into a 5-L 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed 6-hydroxypyrimidine-4-carboxylic acid (100 g, 713.79 mmol, 1.00 equiv) and methanol (2000 mL), followed by the addition of thionyl chloride (210 g, 2.50 equiv) dropwise with stirring at 0°C. The resulting solution was stirred at 30°C for 1 day and concentrated under vacuum to afford 1 15 g (crude) of methyl 6-hydroxypyrimidine-4-carboxylate as an off-white solid. LCMS [M+H]+ 155.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6299-87-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; VERMA, Vishal; SHORE, Daniel; VOLGRAF, Matthew; ESTRADA, Anthony A.; LYSSIKATOS, Joseph; (153 pag.)WO2018/15410; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia