Category: pyrimidines

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.180869-36-7, name is 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine, molecular formula is C8H12N2O2S, molecular weight is 200.26, as common compound, the synthetic route is as follows.Safety of 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine

b 2-Methylthiopyrimidine-4-carboxaldehyde The product of example 1(a) (9.96 g, 50 mmol), and 3 N HCl (42 mL, 126 mmol) were combined and stirred at 48 C. for 16 h, cooled to 23 C., combined with EtOAc (200 mL) and made basic by the addition of solid Na2 CO3 (12.6 g, 150 mmol). The aqueous phase was extracted with EtOAc (4*150 mL, dried (Na2 DO4), concentrated and the residue was filtered through a pad of silica (ca 150 mL) with CH2 Cl2 to afford 7.49 g (97%) of the title compound 1 H NMR (CDCl3): delta 9.96 (s,1), 8.77 (d, 1), 7.44 (d, 1), 2.62 (s,3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,180869-36-7, 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline Beecham Corporation; US6046208; (2000); A;,
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Pyrimidine – Wikipedia

Reference of 696-45-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 696-45-7, name is 4-Amino-6-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step A: 4-Isothiocyanato-6-methoxypyrimidine To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (1.86 g, 7.99 mmol) in dichloromethane at room temperature was added 6-methoxypyrimidin-4-amine (1 g, 8 mmol). The orange solution was stirred at room temperature for 18 hours. The LC/MS showed the desired product as one of the major peaks. The deep orange solution was concentrated and the remaining residue was filtered. The filtrate was purified by silica gel chromatography (10-50percent ethyl acetate/hexanes) to afford 4-isothiocyanato-6-methoxypyrimidine (0.72 g, 4.3 mmol, 54percent yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.49 (1H, d, J=5.79 Hz), 6.95 (1H, d, J=5.79 Hz), 3.92 (3H, s). MS (LC/MS) R.T.=3.15; [M+H]+=168.1.

According to the analysis of related databases, 696-45-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/270405; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5399-92-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation of 1H-Pyrazolo[3,4-d]pyrimidine: 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Pd(OH)2 and are combined in methanol in a reaction vessel. The reaction vessel is evacuated and backfilled with hydrogen gas and the resultant mixture is stirred at rt for several hours. The resultant mixture is filtered and concentrated in vacuo to provide the dehalogenated product, which was used without further purification.

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 5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; ChemoCentryx, Inc.; US2007/10523; (2007); A1;,
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Pyrimidine – Wikipedia

Reference of 1780-40-1 ,Some common heterocyclic compound, 1780-40-1, molecular formula is C4Cl4N2, 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.

In a 250 mL three-neck flask fitted with a degassing tube and temperature probe, acetonitrile (100 mL) and water (25 mL) were degassed with nitrogen for 30 min while stirring. 2,4,5,6-Tetrachloropyrimidine (8.77 g, 0.0402 mol, 1.5 equiv) and triphenylphosphine (0.70 g, 2.6 mmol, 0.1 equiv) were added and degassed for 15 min. 5-Chloro-2-methoxyphenylboronic acid (5.00 g, 0.0268 mol, 1.0 equiv), potassium phosphate (11.39 g, 0.0536 mol, 2.0 equiv) and palladium acetate (301 mg, 1.3 mmol, 0.05 equiv) were added and degassed for 5 min. The reaction was complete after 2 h at room temperature. The reaction mixture was added to 250 mL CH2Cl2. The organic layer was washed twice with water (125 mL), dried over Na2SO4, and concentrated. The crude product was purified by silica gel column chromatography. The product was obtained as a white solid (5.97 g, 69%). 1H NMR (500 MHz, CDCl3, delta): 7.45 (dd, J=8.9, 2.6 Hz, 1H), 7.31 (d, J=2.6 Hz, 1H), 6.94 (d, J=8.9 Hz, 1H), 3.82 (s, 3H); MS (ESI+): calculated for C11H6Cl4N2O, 321.92; m/z found, 323.0 [M+H+].

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. 1780-40-1, 2,4,5,6-Tetrachloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fitzgerald, Anne E.; Liu, Jing; Mani, Neelakandha S.; US2009/76268; (2009); A1;,
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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. 876343-10-1, name is 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClIN3, 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. SDS of cas: 876343-10-1

General procedure: Compound 1a-d or 54 (1 mmol) was mixed with the selected amine, 2-25, (3 mmol) and n-butanol (5 ml) and agitated at145 C for 14-24 h. Then the mixture was cooled to 22 C, dilutedwith water (15 ml) and ethyl acetate (40 ml). After phase separation,the water phase was back extracted with more ethyl acetate(2 10 ml). The combined organic phases were washed with brine(10 ml), dried over anhydrous Na2SO4, filtered and concentrated invacuo, before the crude mixture was purified as specified for eachindividual compound

With the rapid development of chemical substances, we look forward to future research findings about 876343-10-1.

Reference:
Article; Kaspersen, Svein Jacob; Han, Jin; N°rsett, Kristin G.; Rydsa, Line; Kj°bli, Eli; Bugge, Steffen; Bj°rk°y, Geir; Sundby, Eirik; Hoff, Bard Helge; European Journal of Pharmaceutical Sciences; vol. 59; 1; (2014); p. 69 – 82;,
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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.1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, molecular weight is 146.53, as common compound, the synthetic route is as follows.Computed Properties of C4H3ClN2O2

Method 3 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77.0 mmol) was added. The mixture was heated under reflux for 16 hours, left to cool and then poured slowly into water (200 ml) with vigorous stirring. The mixture was stiffed for 1.5 hours and then ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was extracted with a further portion of ethyl acetate (250 ml). The combined extracts were washed with saturated sodium bicarbonate (200 ml) and saturated sodium chloride solution (200 ml), and then dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluding with DCM, to give the product as a yellow liquid (6.37 g, 51%). NMR (CDCl3): 8.62 (s, 1H); MS (MH+): 182, 184, 186.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1820-81-1, 5-Chlorouracil, and friends who are interested can also refer to it.

Reference:
Patent; Pease, Elizabeth Janet; Breault, Gloria Anne; Williams, Emma Jane; Bradbury, Robert Hugh; Morris, Jeffrey James; US2003/149266; (2003); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1060816-58-1, name is 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a suspension of 5-bromo-2-chloro-7H-pyrrolo[2,3-djpyrimidine (0.13 g, 0.50 mmol) and cis-4-.(tert-butyldimethylsilyloxy)cyclohexanol (0.23g, 1.0 mmol) in toluene (8 mL) was added (cyanomethylene)trimethylphosphorane (CMMP; prepared according toChem. Pharm. Bull. 2003, 51(4), 474-476.) (6.3 mL, 0.16 M in THF, 1.0 mmol). The resulting clear solution was refluxed for 16 h. The reaction mixture was washed with brine, and extracted with EtOAc (3X). The combined organic layer was dried (Na2504) and concentrated. The residue was purified on ISCO to provide the desired product (0.16 g, 72%). 1H NMR (400 MHz, CD3OD) oe 8.71 (s, 1H), 7.27 (s, 1H), 4.70 (tt, J = 12.2, 3.9 Hz, 111),3.69 (tt, J = 10.5, 4.2 Hz, 1H), 2.09- 1.99 (m, 3H), 1.86- 1.71 (m, 2H), 1.66- 1.54 (m, 3H),0,90 (s, 9H), 0.08 (s, 6H). MS m/z 444.2 [M+H].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1060816-58-1, 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; EARP, Henry Shelton, III; (109 pag.)WO2017/62797; (2017); A1;,
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Reference of 155-10-2 , The common heterocyclic compound, 155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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.

To a stirred solution of 4-AMINO-2-CHLORO-5-FLUOROPYRIMIDINE (4.22 g, 28. 6 mmol) in anhydrous THF (60 ml) and anhydrous pyridine (8 ml) under nitrogen was added dropwise over 5 min a solution of DI-TERT-BUTYL dicarbonate (15.60 g, 71. 5 mmol) in THF (10 + 2 ml). The solution was stirred at room temperature under nitrogen for 22.25 h. More DI-TERKBUTYL dicarbonate (3.12 g, 14.3 mmol) in THF (2 + 1 ml) was added and the solution was stirred for a further 3 days. The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 15% ETOAC/ISOHEXANE, to leave 14.77 g of a 1: 0. 88 mixture OF DI-TE+BUTYL 2-CHLORO-5-FLUOROPYRIMIDIN-4-YLIMIDODICARBONATE and DI-TE+BUTYL dicarbonate as a white solid.

The synthetic route of 155-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 936643-80-0, name is 2-(Chloromethyl)pyrimidine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 936643-80-0

First Step A solution of 4-nitro-m-cresol (0.25 g, 1.6 mmol), 2-(chloromethyl)pyrimidine hydrochloride (0.40 g, 2.4 mmol) and potassium carbonate (0.50 g, 4.0 mmol) in N,N-dimethylformamide (6.0 mL) was stirred at 70 C. for 18 h. Cooled to ambient temperature, the reaction mixture was poured into ice water, extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford 2-[(3-methyl-4-nitrophenoxy)methyl]pyrimidine as crude material (0.32 g, y. 81%) as solid. 1H NMR (DMSO-d6) delta (ppm) 8.84 (d, J=4.92 Hz, 2H), 8.03 (d, J=9.08 Hz, 1H), 7.48 (t, J=4.90 Hz, 1H), 7.10 (d, J=2.68 Hz, 1H), 7.00 (dd, J=2.80, 9.12 Hz, 1H), 5.43 (s, 2H), 2.53 (s, 3H); LCMS (m/z): 246.4 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 936643-80-0, 2-(Chloromethyl)pyrimidine hydrochloride.

Reference:
Patent; CARNA BIOSCIENCES, INC.; SBI BIOTECH CO., LTD.; Irie, Takayuki; Sawa, Ayako; Sawa, Masaaki; Asami, Tokiko; Funakoshi, Yoko; Tanaka, Chika; US2014/18533; (2014); A1;,
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Reference of 4983-28-2, 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.4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, molecular weight is 130.53, as common compound, the synthetic route is as follows.

0.80 mg (6.13 mmol) 2-chloro-5-hydroxypyrimidine, 1.26 g (9.19 mmol) 1-bromo-2-methylpropane and 1.69 g (12.26 mmol) K2CO3 are added to 10 mL DMF and stirred at 80° C. over night. Afterwards the reaction is quenched by the addition of water and extracted with EtOAc. The org. layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo.C8H11ClN2O (M=186.6 g/mol)ESI-MS: 187 [M+H]+Rt (HPLC): 1.04 min (method D)

The chemical industry reduces the impact on the environment during synthesis 4983-28-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEIMANN, Annekatrin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/315882; (2014); A1;,
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