Category: pyrimidines

Synthetic Route of 209959-33-1, 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. 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine, molecular formula is C14H20BrN3O4, 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 15 tert-Butyl 5-bromopyrimidin-2-ylcarbamate 11 To a solution of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine 10 (216 kg crude, 460 mol, assuming quantitative yield in previous step) in anhydrous ethanol (1692 L) was slowly added a solution of sodium hydroxide (55.2 kg, 1380 mol) in water (344 L) while maintaining the temperature at 0-20 C. The mixture was stirred at that temperature until the content of 2-[bis(tert-butoxycarbonyl)-amino]-5-bromopyrimidine (10) was ?0.5% by HPLC. The reaction mixture was cooled to 0-5 C. and the pH was adjusted to 7 by addition of oxalic acid (86.0 kg, 955 mol) while maintaining the temperature below 5 C. The mixture was then distilled under vacuum to a volume of 500-600 L while controlling the temperature below 50 C. Water (800 kg) was added and the mixture was stirred for 1 h. The solid was collected by filtration and stirred with water (2*500 L). The resulting solid was collected by filtration and dried under reduced pressure at 50 C. to afford tert-butyl 5-bromopyrimidin-2-ylcarbamate 11 (107 kg, 85% yield over two steps). 1H NMR (500 MHz, CDCl3) delta 8.63 (s, 2H), 8.12 (s, 1H), 1.55 (s, 9H). LCMS (ESI) m/z [M+H-Boc] 176

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 209959-33-1, 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine.

Reference:
Patent; Genentech, Inc.; Babu, Srinivasan; Cheng, Zhigang; Gosselin, Francis; Hidber, Pirmin; Hoffmann, Ursula; Humphries, Theresa; Reents, Reinhard; Tian, Qingping; Yajima, Herbert; US2014/100366; (2014); A1;,
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Electric Literature of 85989-61-3 ,Some common heterocyclic compound, 85989-61-3, molecular formula is C6H3Cl2N3, 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 16A; 6-({2-[(7-Chloroimidazo[1,2-c]pyrimidin-5-yl)amino]ethyl}amino)nicotinonitrile 707 mg (3.20 mmol) of 5,7-dichloroimidazo[1,2-c]pyrimidine (Example 11A) are suspended in 25 ml of 2-propanol, and 1.35 g (3.52 mmol) of 6-[(2-aminoethyl)amino]nicotinonitrile trifluoroacetate (Example 13A) and 1.03 g (7.99 mmol) of DIPEA are added. The mixture is heated at 80 C. for 16 h. After this time, water is added and the precipitate which has separated out is filtered off with suction. It is washed with a little 2-propanol/water and the resulting solid is dried under high vacuum. 523 mg (50% of theory) of the product are obtained.LCMS (method 3): Rt=1.31 min. (m/z=314 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.37 (d, 1H), 8.33 (t, 1H), 7.93 (s, 1H), 7.80 (s, 1H), 7.68 (d, 1H), 7.50 (d, 1H), 6.90 (s, 1H), 6.56 (s, br, 1H), 3.62 (m, 2H), 3.31 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,85989-61-3, its application will become more common.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/113441; (2010); A1;,
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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. 289042-10-0, name is N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, molecular formula is C28H29FN3O3PS, 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. category: pyrimidines

A mixture of DPPO (19.17 g) and THF (227 ml) were warmed briefly to 40 C. until a clear solution had formed then inerted by the sequential application of vacuum and nitrogen (5 cycles). The mixture was immersed in an acetone/CO2 bath cooling the contents to -75 C. Sodium bis(trimethylsilyl)amide (37.4 ml of 1.0 M solution in THF) was added to the reaction mixture over 10 minutes from a pressure equalising dropping funnel maintaining the temperature below -74 C and forming a red solution of the anion. THF (10 ml) was rinsed through the dropping funnel into the mixture and the mixture stirred a further 1 hour at -76 C forming a red suspension. BFA (80 ml of 13.5% w/w toluene solution) was added in portions to the suspension over 20 minutes from a pressure equalising dropping funnel maintaining the temperature below -73 C. Toluene (20 ml) was rinised through the dropping funnel into the mixture and the mixture stirred a further 15 minutes at -76 C. The chilling bath was lowered and the suspension allowed to warm to 10 C over 1.5 hours. Glacial acetic acid (3.21 g) in water (15 g) was added in one portion raising the temperature to 18 C and dissolving all solids and the mixture was stirred a further 5 minutes. The mixture was concentrated by distillation at atmospheric pressure (jacket 110 C) to a temperature of 94 C collecting a total of 274 ml distillates. The concentrated mixture was cooled to 40 C, water (40 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. Sodium hydrogen carbonate (2.99 g) in water (40 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. Water (30 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. The organic phase was transferred to a distillation apparatus with toluene (20 ml) and concentrated by distillation at atmospheric pressure (jacket 125-130 C) to a temperature of 116 C collecting 85 ml distillates. Vacuum was applied (400-500 mbar) and a further 16.5 ml distillates collected to a temperature of 111 C. The vacuum was released and the concentrated mixture allowed to cool to 80 C. Warm MeOH (140 ml, 50 C) was added with rapid stirring and the batch allowed to self-cool to 20 C over 30 minutes during which time a solid was deposited. The suspension was further cooled to 2 C for 30 minutes then the solid was collected by filtration on a sinter and pulled as dry as possible. The solid was washed with cold MeOH (60 ml, 2C.) and again pulled as dry as possible then transferred to a vacuum oven and dried overnight (50 C, 200 mbar); giving BEM (14.01 g, 67.7%). 1H NMR (CDCl3, 270 MHz) 7.65 [m, 2H, ArH], 7.09 [m, 2H, ArH], 6.52 [dd, 1H, ArCH=CH], 5.47 [dd, 1H, ArCH=CH], 3.57, 3.50 [2 x s, 6H, NCH3, SO2CH3], 3.38 [hept., 1H, ArCHMe2], 2.45, 2.30 [2x dd, 2H, CH2CO2tBu], 1.55, 1.13 [dt, dd, 2H, acetonide CH2], 1.50, 1.40 [2x s, 6H, acetonide C(CH3)2], 1.45 [s, 9H, CO2C(CH3)3], 1.27 [dd 6H, ArCH(CH3)2]

With the rapid development of chemical substances, we look forward to future research findings about 289042-10-0.

Reference:
Patent; AstraZeneca AB, AstraZeneca AB; Shionogi & amp Co., Ltd.; US2004/49036; (2004); A1;,
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Reference of 1122-47-0, 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. 1122-47-0, name is 4-Amino-1-methylpyrimidin-2(1H)-one. A new synthetic method of this compound is introduced below.

To a water solution (5 mL) of 1-Methylcytosine (1-Mecyt) (0.025 g, 0.2 mmol) was added dropwise and under stirring, an aqueous solution of BaCl2·2H2O (0.049 g, 0.2 mmol) at 60 C.The colorless mixture was left to evaporate and afforded colorless crystals within 2-3 days, upon very slow evaporation at room temperature. Yield: 65%; IR (KBr, nu/cm-1): 3421, 3326,3245, 3155 (O-H), 2911 (C-H), 1665, 1632, 1630, 1570 (C=O). Anal. Calcd for C5H9N3O2Cl2Ba(350.91 g mol-1): C, 17.09; H, 2.58; N, 11.96%. Found C, 17.89; H, 2.92; N, 10.99%. Compound 2 was prepared following the same synthetic protocol as for 1 using an aqueous solution(5 mL) of BaBr2·2H2O (0.067 g, 0.2 mmol). Yield: 65%; IR (KBr, nu/cm-1): 3420, 3321, 3236, 3149(O-H), 2907 (C-H), 1670, 1639, 1622, 1569 (C=O). Anal. Calcd for C5H9N3O2Br2Ba (440.28 gmol-1): C, 13.64; H, 2.06; N, 9.54%. Found C, 13.24; H, 2.50; N, 9.05%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1122-47-0, 4-Amino-1-methylpyrimidin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Article; Marino, Nadia; Bruno, Rosaria; Armentano, Donatella; De Munno, Giovanni; Journal of Coordination Chemistry; vol. 71; 6; (2018); p. 828 – 844;,
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Related Products of 890094-38-9, 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. 890094-38-9, name is 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine, molecular formula is C7H9ClN4O2, 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.

4-(2-morpholinoethoxy)phenylamine(4.4g) was added to a solution of Compound 2-3(4.3g) in n-butanol(150ml). The mixture was reacted at 90C for 3.5 hours, cooled to room temperature, filtered, washed and dried to obtain a red solid(6.4g) in a yield of 80.0%. MS m/z(ESI): 403[M+H]+.

According to the analysis of related databases, 890094-38-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
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Electric Literature of 1266343-30-9, 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. 1266343-30-9, name is 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C7H5BrClN3, 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.

Stir a suspension of 5-bromo-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (454 g 1.84 mol) in ammonia (30% in H20, 3.63 L) at 120 C in a Hastelloy pressure vessel for 18 h. Cool to 20 C, filter, wash with H20 (1.80 L) and methanol (900 mL), and dry to give the title compound (351 g, 82%) as a white solid. ES/MS m/z (79Br) 227.2(M+H).

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 1266343-30-9, 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; ELI LILLY AND COMPANY; CIFUENTES-GARCIA, Marta Maria; GARCIA-PAREDES, Maria Cristina; (34 pag.)WO2018/194885; (2018); A1;,
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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 175277-33-5, name is 4-(Dimethoxymethyl)-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-(Dimethoxymethyl)-2-methylpyrimidine

4-Dimethoxymethyl-2-methyl-pyrimidine (4.5 g, 26.7 mmol) was added to a solution of HBr (48% in H2O, 10 niL) and stirred at room temperature for 2 hours. It was then diluted with water and washed with diethylether (2x). The aqueous layer was carefully neutralized with saturated sodium carbonate and extracted with ethyl acetate (2x). The combined extracts were dried over MgSO4. 2-Propanol (100 mL) was added. To this solution, aniline (2.5 mL, 26.7 mmol) was added and followed with diphenylphosphite (5.1 mL, 26.7 mmol). The reaction mixture was stirred at room temperature overnight and then concentrated. The residue was purified on silica gel column with 20% ethyl acetate/CH2Cl2 to give a yellow solid (3.3 g, 29% for 2 steps) as the desired product. MS (ESP+) m/z 432.2 (M + 1).

With the rapid development of chemical substances, we look forward to future research findings about 175277-33-5.

Reference:
Patent; BIOGEN IDEC MA INC; WO2006/26305; (2006); A1;,
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Electric Literature of 13053-88-8, 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 13053-88-8, name is N-(Pyrimidin-2-yl)acetamide. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: For complexes 1-8, a warm solution of ca. two equivalents of ligand (0.151 mmol) in absolute EtOH (10 cm3) was added to a warm solution of [Cd(tsac)2(H2O)] (0.040 g, 0.076 mmol) in absolute EtOH (10 cm3). The mixture was heated to reflux for 3 h. After cooling to room temperature it was filtered and evaporated to half volume. Further slow evaporation of EtOH over several days gave a yellow solid which was collected, washed with absolute EtOH anddried under vacuum

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 13053-88-8, N-(Pyrimidin-2-yl)acetamide.

Reference:
Article; Al-Jibori, Subhi A.; Al-Bayati, Mohamed M.A.; Gergees, Hayfa M.; Wagner, Christoph; Hogarth, Graeme; Inorganica Chimica Acta; vol. 459; (2017); p. 73 – 79;,
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Electric Literature of 1480-66-6 ,Some common heterocyclic compound, 1480-66-6, molecular formula is C5H3ClF3N3, 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.

Key Intermediate 5 fljit-5″): (6-Chloro-24rifluoromethyl-pyrimidin-4-ylV[“5-(3-ethoxy- benzenesulfonyl)-thiazol-2-vn-amine[0114] A mixture of 4-amino-6-chloro-2-trifluoromethyl-pyrimidine [(Inoue, S. et al, J.Org. Chem., 1961, 26, 4504) 185 mg, 0.94 mol] and NaH (60% dispersion in mineral oil, 40 mg, 1.0 mmol) in DMF (4.0 mL) was stirred, under Ar, at RT for 30 min. A solution of Intl -A (326 mg, 0.94 mmol) in DMF (2.0 mL) was added. The reaction mixture was stirred at RT for 30 min and was heated at 55 0C for Ih. Additional NaH (60% dispersion in mineral oil, 20 mg, 0.05 mmol) was added, and the reaction mixture was heated at 55 0C overnight. Additional NaH (60% dispersion in mineral oil, 20 mg, 0.05 mmol) was added, and the reaction mixture was heated at 55 0C for 1 h. The reaction mixture was cooled to RT and partitioned between EtOAc (ca. 100 mL) and water (ca. 25 mL). The layers were separated and the organic phase was washed with saturated aqueous NaCl (I x 100 mL), dried (Na2SO4), and concentrated under reduced pressure to give an oil. This oil was purified by flash chromatography, elution with 25-75% EtOAc in hexanes, to give Int-5 (182 mg, 42%) as a foam. LCMS (m/z): 465, 467 (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. 1480-66-6, 6-Chloro-2-(trifluoromethyl)pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ICAGEN, INC.; WO2007/75852; (2007); A2;,
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Application of 831203-15-7, 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 831203-15-7, name is 2-(5-Bromopyrimidin-2-yl)acetonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2- (5-bromopyrimidin-2-yl) acetonitrile (0.1 (^, 0.50%)4-fluorophenylboronic acid (0.088, 0.601111111)Potassium carbonate (0.21 g, 1.50 mmol),Tetrakis (triphenylphosphine) palladium (0.3 g, 0.30 mmol)And toluene (10 mL) were successively added to a 50 mL reaction flask,The reaction was carried out with nitrogen and the reaction was carried out at 100 C for 8 hours.The reaction was quenched and the solvent was removed by distillation under reduced pressure. The remaining solid was extracted with dichloromethane (10 mL X), washed with organic phase, saturated brine (20 mL) and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The title compound (white solid, 0.088, 80.1%) was obtained by silica gel column chromatography (petroleum ether / acetone (nu / nu) = 20/1)

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 831203-15-7, 2-(5-Bromopyrimidin-2-yl)acetonitrile.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Wei Dehuo; Xue Yaping; Zhang Yingjun; (44 pag.)CN106674207; (2017); A;,
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