Triethylamine → 2-methyl-N-[4-methyl-2-[2-[(trifluoromethyl)thio]-4-pyrimidinyl]phenyl]propanamide
Reaction equation
[F:1][C:2](I)([F:4])[F:3].[SH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[CH:10]=[CH:9][N:8]=1.C(N(CC)CC)C>C(#N)C.CCOCC>[CH3:23][CH:22]([CH3:24])[C:21]([NH:20][C:14]1[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[C:11]1[CH:10]=[CH:9][N:8]=[C:7]([S:6][C:2]([F:4])([F:3])[F:1])[N:12]=1)=[O:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
2 g trifluoromethyl iodide was condensed into a solution of 0.57 g (0.002 mol) N-[2-(2-mercapto-4-pyrimidinyl)-4-methylphenyl]-2-methylpropanamide and 2.5 g triethylamine in 20 mL anhydrous acetonitrile, and the reaction mixture was stirred under a dry ice condenser while exposed to a sun lamp for 4 h. The reaction mixture was diluted with 100 mL ether and washed successively with water, 1N sodium hydroxide solution, and brine. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.52 g of the title compound as yellow crystals melting at 114°-116° C. 1H NMR (CDCl3): δ 1.21 (d,6H), 2.40 (s,3H), 2.55 (m,1H), 7.40-8.70 (5H), 10.7(s,1H,NH).
Workup
- washwashed successively with water, 1N sodium hydroxide solution, and brine
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
- customThe crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent
Sources & evidence
- ORD record
- ord-0109d0ca322846629b0e04a49894fff5
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05631206
Reaction notes
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