Pyrimidines

Reference of 573675-31-7 ,Some common heterocyclic compound, 573675-31-7, molecular formula is C7H3BrClN3, 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.

Step 1: 7-bromo-N-(2-methylbiphenyl-3-yl)pyrido[3,2-d]pyrimidin-4-amine To a vial was added 2-methylbiphenyl-3-amine (Example 1, Step 1: 0.4 g, 2.18 mmol), 7-bromo-4-chloropyrido[3,2-d]pyrimidine (Ark Pharm, cat#AK-27560: 540 mg, 2.2 mmol), and isopropyl alcohol (10. mL) The mixture was heated to 110 C. for 4 h. The mixture was cooled to room temperature, concentrated, and the crude product was used directly in the next step without further purification. LC-MS calculated for C20H16BrN4 (M+1)+: m/z=391.1; found 391.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,573675-31-7, its application will become more common.

Reference:
Patent; Incyte Corporation; Lajkiewicz, Neil; Wu, Liangxing; Yao, Wenqing; (58 pag.)US2017/174679; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 187035-79-6, Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, 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, Product Details of 187035-79-6, blongs to pyrimidines compound. Product Details of 187035-79-6

Example 13 (R)-(2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol and (S)-(2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol To a solution of (R)-methyl 1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (80 mg, 0.228 mmol) in iPrOH (2 mL) and DCM (1 mL) was added ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (174 mg, 0.684 mmol) and DIEA (177 mg, 1.37 mmol). The mixture was stirred at 60 C. overnight. Water (5 mL) was added to the mixture and the aqueous layer was extracted with EtOAc (2*10 mL). The combined organic layers were washed with water (2*10 mL) and brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford (R)-methyl 2-(5-(ethoxycarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl)-1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (75 mg, 57.8% yield) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,187035-79-6, Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; (82 pag.)US2016/113930; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 96833-41-9, 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 96833-41-9, name is 2-Chloro-4-methoxypyrimidin-5-amine. This compound has unique chemical properties. The synthetic route is as follows.

In a Shlenck reactor, a solution of 6-chloro-2-methoxy-3-nitropyridine (1.00 g, 5.30mmol), 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (1.23 g, 5.83 mmol) andK3P04 (3.38 g, 15.90 mmol) in 1,4-dioxane (44 mL) and distilled water (9 mL) was degassed under N2. [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium (II), complex with dichloromethane (434.00 mg, 0.53 mmol) was added, the mixture was degassed again under N2 and heated at 80 C for 4 h. The mixture was extended withEtOAc and filtered on a pad of celite. The cake was washed with EtOAc and water. The layers were separated and the organic layer was dried over Mg504, filtered off and evaporated in vacuo to give a brown solid. The residue was purified by column chromatography on silica gel (irregular SiOH, 15-40 jim, 50 g, dry loading on celite, mobile phase: heptane/EtOAc, gradient: 95:5 to 60:40) to give 922 mg of intermediate138 (74% yield, yellow solid).

According to the analysis of related databases, 96833-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 302964-08-5 ,Some common heterocyclic compound, 302964-08-5, molecular formula is C16H13Cl2N5OS, 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 21; Procedure for the Preparation of Dasatinib Form L2A mixture of compound 1 (0.50 g, 1.27 mmol), N-(2-hydroxyethyl)piperazine (0.33 g, 2.54 mmol) and N-ethyldiisopropylamine (0.43 ml, 2.54 mmol) in DMSO (1.3 ml) was stirred at 80-85 C. for 2 hours. Butan-2-ol (7 ml) was slowly added at this temperature. The solution was slowly cooled to 0-5 C. The product was filtered off, washed with butan-2-ol (10 ml) and dried on the filter, than dried under reduced pressure at 40 C. for 6 hours. Yield: 0.56 g.

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. 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 38275-55-7, 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. 38275-55-7, name is 5-Fluoropyrimidine-2-carbonitrile, molecular formula is C5H2FN3, 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.

A round-bottom-flask containing 5-fluoropyrimidine-2-carbonitrile (Method 59, 1.50 g, 12.19 mmol) was charged with anhydrous THF (30 ml) under N2. The solution was cooled to 0 C, and a solution of MeMgBr (4.90 ml of a 3.0 M solution in ether, 14.62 mmol) was added dropwise. After 2 hours at 0 C, the reaction mixture was quenched with ice water and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness to give the title compound as an oil (0.778 g, yield 46%). GC-MS, 140 (M); 1H NMR (CDCl3) delta 8.65 (s, 2H), 2.65 (s, 2H).

According to the analysis of related databases, 38275-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 1211443-58-1, name is 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C12H12ClN3O2

2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (1.07g, 4.03mmol), HBTU (1.53g, 4.03mmol) and diisopropylethylamine (2mL, 12.1mmol) are dissolves in dimethylformamide (20 mL). 2 M solution of dimethylamine in ethanol (2.4mL, 4.8 mmol) is added and the mixture is stirred for 30 minutes to achieve complete conversion. The reaction mixture is diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate, water, then brine. The organic phase is dried (Na2SC^), filtered and concentrated. Purification by chromatography on silicagel(ethyl acetate :heptane) provides 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6- carboxylic acid dimethylamide (927mg,79% yield) MS(ESI) m/z 293.1 (M+H)+

With the rapid development of chemical substances, we look forward to future research findings about 1211443-58-1.

Reference:
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LTD.; BESONG, Gilbert; BRAIN, Christopher Thomas; BROOKS, Clinton A.; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; HE, Guo; HOU, Ying; HOWARD, Steven; LI, Yue; LU, Yipin; MORTENSON, Paul; SMITH, Troy; SUNG, Moo; WOODHEAD, Steven; WRONA, Wojciech; WO2010/20675; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5466-43-3, 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 5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[00571] To a solution of 2,4-dichloro-5H,6H,7H-cyclopenta[d]pyrimidine (3 g, 15.87 mmol) in THF (15 mL) was added 6M aq NaOH solution (10 eq, 26.45 ml) and the reaction stirred at 50 C for 48 h. The reaction mixture was concentrated in vacuo to remove the organic solvent. The resulting aqueous solution was acidified to pH 4 with 5M aq HC1 solution and extracted with EtOAc (2 x 50 ml), dried over sodium sulfate and concentrated in vacuo to afford the title compound (2.09 g, 75%) as a pale orange powder. [00572] Method B: LC-MS m/z = 170.9 [M + H]+; RT = 0.68 min.

According to the analysis of related databases, 5466-43-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); 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.4316-98-7, name is 6-Chloro-4,5-diaminopyrimidine, molecular formula is C4H5ClN4, molecular weight is 144.56, as common compound, the synthetic route is as follows.Product Details of 4316-98-7

EXAMPLE 101 6-Chloro-8-(2,4-dimethoxy-5-bromo-phenyl)-purine Prepared analogously to Example 14 from 4,5-diamino-6-chloropyrimidine and 2,4-dimethoxy-5-bromo-benzoic acid. M.p.: 260-263 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-98-7, 6-Chloro-4,5-diaminopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Dr. Karl Thomae GmbH; US4722929; (1988); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 6214-65-9, name is 5-Acetyluracil. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6N2O3

A suspension of 5-acetyluracil (3.1 g, 20 mmol), and potassium carbonate (6.9 g, 50 mmol) in DMF (75 ml) was stirred for 20 min. Then benzyl bromide (6.0 ml, 50 mmol) was added. The resulting mixture was stirred for 8 h at room temperature. DMF was distilled under vacuum. The residue was purified by column (dichloromethane:methanol 40:1). The appropriate fraction was concentrated and crystallized from ethanol to afford 5.34 g of a white solid. Yield was 79.8%. Mp. 92-93 C. 1H-NMR (CDCl3): 8.23 (s, 1H), 7.29-7.49 (m, 10H), 5.17 (s, 2H), 5.01 (s, 2H), 2.62 (s, 3H). 13C-NMR (CDCl3): 194.5, 160.7, 151.0, 148.4, 136.2, 134.4, 129.2, 129.0, 128.9, 128.5, 128.2, 127.8, 112.2, 53.4, 44.9, 30.7. FAB-HRMS: [M+H]+ calcd. for C20H19N2O3 335.1396, found 335.1412.

With the rapid development of chemical substances, we look forward to future research findings about 6214-65-9.

Reference:
Patent; Nair, Vasu; Chi, Guochen; Uchil, Vinod R.; US2006/223834; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3438-46-8, 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.3438-46-8, name is 4-Methylpyrimidine, molecular formula is C5H6N2, molecular weight is 94.1145, as common compound, the synthetic route is as follows.

[00125] In one example, Compound iii was prepared by reacting 4- (bis(hydroxyethyl)amino)benzaldehyde (234 mg, 1.12 mmol) with of -4-methylpyrimidine (112 mu,, 1.23 mmol) and of potassium tert-butoxide (376 mg, 3.35 mmol) in N,N-dimethyl formamide (10 mL) for 12 hours at 80 C. The resulting mixture was cooled to ambient temperature and filtered through celite and concentrated. Compound iii was isolated as the major component of a mixture by silica gel chromatography using an ethyl acetate/methanol/hexane solvent system. (E)-2,2′-{[4-(2-(pyrimidin-4- yl)vinyl)phenyl]azanediyl}diethanol (Compound iii): 1H NMR (MeOD, 600 MHz) delta 9.02 (d, J=1.2 Hz, 1H), 8.61 (d, J= 5.4 Hz, 1H), 7.88 (d, J= 15.6 Hz, 1H), 7.58 (d, J= 8.7 Hz, 2H), 7.53 (dd, J= 6.0, 1.2 Hz, 1H), 6.98 (d, J= 15.6 Hz, 1H), 6.88 (d, J= 8.7 Hz, 2H), 3.71 (t, J= 6.0 Hz, 4H), 3.57 (t, J= 6.0 Hz, 4H); 13C NMR (DMSO-d6, 150 MHz) delta 165.23, 159.17, 157.76, 149.72, 139.99, 130.84, 125.87, 121.64, 119.42, 113.66, 51.36, 50.08; HRMS clcd for C16H19N302+m/z (M+H)+ 286.1550, found 286.1546.

Statistics shows that 3438-46-8 is playing an increasingly important role. we look forward to future research findings about 4-Methylpyrimidine.

Reference:
Patent; TEXAS CHILDREN’S HOSPTIAL; ANNAPRAGADA, Ananth; TANIFUM, Eric A.; SRIVASTAVA, Mayank; (143 pag.)WO2016/57812; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia