Category: 147118-37-4

147118-37-4, 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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, molecular formula is C16H18FN3O3S, 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 19 Preparation of 2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (3) 2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-2,2-dimethyl-6-((1-phenyl-1H-tetrazol-5-ylsulfonyl)methyl)-1,3-dioxan-4-yl)acetate (25.75 g) prepared in Example 15 and N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (15.55 g) were dissolved in tetrahydrofuran (60 ml), followed by cooling to -78 C. under an argon atmosphere, and lithium bis(trimethylsilyl)amide (120 of a 0.5M solution in tetrahydrofuran) was added thereto over 10 minutes, followed by stirring at the same temperature for 2 hours. Then, the mixture was stirred for 4 hours while warming to 0 C. A saturated ammonium chloride aqueous solution (250 ml) was added to the reaction liquid, followed by stirring for 10 minutes, and ethyl acetate (500 ml) was added thereto. The organic layer was separated and washed successively with purified water (250 ml), a saturated sodium bicarbonate aqueous solution (250 ml,) and a saturated sodium chloride aqueous solution (250 ml), dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting solid was stirred with isopropyl ether, filtered and collected. This solid was dried in a vacuum oven overnight (50 C., 200 mbar) to give the title compound (26.06 g, 90%). 1H-NMR (400 MHz, CDCl3) delta 7.66-7.63 (m, 2H), 7.29-7.05 (m, 7H), 6.52-6.48 (dd, 1H), 5.48-5.43 (dd, 1H), 4.43-4.37 (m, 1H), 4.32-4.21 (m, 1H), 3.60 (s, 3H), 3.53 (s, 3H), 3.39-3.36 (m, 1H), 3.12-2.99 (dd, 2H), 2.50-2.27 (m, 2H), 1.51-1.37 (m, 14H), 1.28-1.10 (m, 7H)

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. 147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lee, Hongwoo; Park, Daejong; Yoo, Choongleol; Nam, Donghyuk; Ryu, Hohyung; Kim, Dongjin; US2012/136151; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

147118-37-4, 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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE-6PREPARATION OF tert-BUTYL 2-[(4R,6-2,2-DIMETIIYL-6-[(E)-2-[4-(4- FLUOROPHENYL)-6-ISOPROPYL-2-[N-METHYL(N-METHYLSULFONYL)-AMINOIPYRIMIDIN-5-YL]VINYLI-1,3-DIOXAN-4-YLIACETATE [DIPROTECTED ROSUVASTATIN)A mixture of 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl arnino)pyrimidine-5-ylcarboxaldehyde (50 g, 0.142 mole) and chiral diol sulphone (62.82 g, 0.142 mole) was dissolved in tetrahydrofuran (750 ml) at 40-45C. The above reaction mass was cooled to -75 to -80C and thereafter potassium tertbutoxide (22.33 g, 0.199 mole) was dissolved in tetrahydrofuran (100 ml) slowly at -80C to -75C over a period of 45 mi Stirring was continued till pyrimidine carboxaldehyde was consumed (-1 h) and the progress of reaction was monitored by HPLC. After completion of the reaction, 20% aqueous ammonium chloride solution (500 ml) was added to the reaction mass at -75 to -80C. Thereafter, temperature was raised to 20-30C. The product was extracted with ethyl acetate (2 x 250 ml), washed with 10% w/w aqueous sodium chloride (500 ml) and solvent was evaporated under reduced pressure at 40-45C. Thereafter, methanol (750 ml) was added to the concentrated mass and heated to 60-65C to obtain a clear solution. It was cooled to 0-5C and the title compound was isolated by filtration.Yield: 65 gChroinatographic Purity (by HPLC): 99%

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 147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide.

Reference:
Patent; AUROBINDO PHARMA LIMITED; NANDI, Sukumar; HANDA, Vijay Kumar; GONA, Balanarasimha Reddy; KANKANALA, Shanthan Kumar Reddy; MEENAKSHISUNDERAM, Sivakumaran; WO2014/108795; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. A new synthetic method of this compound is introduced below., 147118-37-4

Example 10. [262] E-(6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide [263] 2-[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (5.4 g), N-[4-(4-fluorophenyl)-5-formyl-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (3.9 g), and tetrahydrofuran (54 mL) were added to a reactor and then the reaction mixture was cooled to -70C. A solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 15.0 mL) was slowly added to the reaction mixture, the temperature of which was then adjusted to -20?-10C. The reaction mixture was stirred for 1 hours and then 8% sodium bicarbonate solution (100.0 mL) was added under stirring. The separated organic layer was washed with water (100.0 mL) and then concentrated under reduced pressure to obtain E-(6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide as a solid (5 g, yield 80%).[264] 1H-NMR, 400 MHz, CDCl3, ppm : 1.23~1.27(m, 7H), 1.40(s, 3H), 1.50(s, 3H), 2.42~2.80(dd, 2H), 3.20(s, 3H), 3.37(q, 1H), 3.51(s, 3H), 3.57(s, 3H), 3.70(s, 3H), 4.41(m, 2H), 5.44(dd, 1H), 6.49(d, 2H), 7.08(t, 2H), 7.64(q, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; YUHAN CORPORATION; JU, Hyun; JOUNG, Sang-Sun; YI, Hyun-Jik; KHOO, Ja-Heouk; LIM, Jong-Chul; KIM, Jae-Gyu; WO2012/2741; (2012); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

147118-37-4, 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 147118-37-4 as follows.

Example 7 Preparation of Compound of Formula (8B2) [0152] [0153] 2.5 g aldehyde compound, 3.6 g chiral diol sulfone (1a-B) and 50 mL THF were taken in round bottom flask at 35 C. under nitrogen atmosphere. The reaction mixture was cooled to -70 C. to -78 C. and treated with 10 g of NaH. The reaction mixture was stirred for 7-8 hours and quenched with ammonium chloride after completion of the reaction as monitored by TLC. The layers were separated at room temperature followed by washing organic layer with saturated sodium 38 mL saturated sodium bicarbonate solution. The organic layer was distilled under vacuum below 50 C. The solid residue 7.1 g was treated with 35 mL methanol and heated at 55 C. for 1 hour, cooled back to 0 C. and stirred for 1 hour. The isolated product was filtered and washed with chilled methanol to obtain 2.8 g compound of Formula (8B2). [0154] The above process can be repeated by using chiral diol sulfone of Formula (1a-A), (1a-C), (1a-D) for preparing the compound of Formula (8B1), (8B3) and (8B4) respectively by replacing the compound of Formula (1a-B).

The chemical industry reduces the impact on the environment during synthesis 147118-37-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dwivedi, Shriprakash Dhar; Patel, Dhimant Jasubhai; Rupapara, Mahesh Laljibhai; US2013/158263; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia