N-[5-(chloromethyl)-4-(4-fluorophenyl)-6(1-methylethyl)-2-pyrimidinyl ]-N-methyl- Methanesulfonamide synthesis
- Product Name:N-[5-(chloromethyl)-4-(4-fluorophenyl)-6(1-methylethyl)-2-pyrimidinyl ]-N-methyl- Methanesulfonamide
- CAS Number:925422-06-6
- Molecular formula:C16H19ClFN3O2S
- Molecular Weight:371.86
![4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol](/CAS/GIF/147118-36-3.gif)
147118-36-3
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Yield:925422-06-6 88%
Reaction Conditions:
with methanesulfonyl chloride;triethylamine in dichloromethane at 0 - 25; for 5 h;
Steps:
2
Preparation 2. [175] N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide [176] N-[4-(4-fluorophenyl)-5-hydroxymethyl-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (50.0 g), dichloromethane (250.0 mL), and triethylamine (47.3 mL) were added to a reactor and then the reaction mixture was cooled to 0～5 °C. Methanesulfonyl chloride (13.2 mL) was slowly added to the reaction mixture, which was then stirred at 20～25°C for 5 hours. Water (100.0 mL) was added to the reaction mixture. The separated organic layer was sequentially washed with 0.5N hydrochloric acid solution (100.0 mL) and then water (100.0 mL). The organic layer was concentrated under reduced pressure to remove the solvent. n-Hexane (150.0 mL) was added to the resulting residue under stirring. The resulting suspension was filtered under reduced pressure. The resulting white solid was dried to obtain N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (45.5 g, yield 88%).[177] 1H-NMR, 400 MHz, CDCl3, ppm : 1.35(d, 6H), 3.48(m, 1H), 3.50(s, 3H), 3.57(s, 3H), 4.58(q, 2H), 7.22(t, 2H), 7.80(q, 2H)
References:
WO2012/2741,2012,A2 Location in patent:Page/Page column 18-19
![4-(4-Fluorophenyl)-6-isopropyl-2-[(Methanesulfonyl)MethylaMino]pyriMidine-5-carboxylic acid ethyl ester](/CAS/20150408/GIF/147118-30-7.gif)
147118-30-7
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![Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine-5-carboxylate](/CAS/GIF/289042-11-1.gif)
289042-11-1
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