Pyridine → 2-methyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide
Reaction equation
C(Cl)(=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([S:22][CH3:23])[N:17]=2)[CH:10]=1.N1C=CC=CC=1.CC[O:32]CC>C(Cl)(Cl)Cl>[CH3:5][CH:3]([CH3:4])[C:2]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH3:8])=[CH:10][C:11]=1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([S:22][CH3:23])[N:17]=1)=[O:32]Participants
Procedure
A solution of 11.7 g (0.11 mol) isovaleryl chloride in 15 mL dry chloroform was added dropwise with stirring to a solution of 23.1 g (0.10 mol) 4-methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamine and 12 g pyridine in 60 mL dry chloroform. Stirring was continued for 1 h at room temperature, after which the reaction mixture was diluted with 200 mL ether and washed successively with water, 0.5N hydrochloric acid solution, and brine. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 10:1 chlorobutane/ethyl acetate mixture as eluent to yield 28.3 g of the title compound as white crystals melting at 134°-135° C. 1H NMR (CDCl3): δ 1.23 (d,6H), 2.30 (s,3H), 2.40 (s,3H) 2.47 (m,1H), 7.40-8.6 (5H), 10.7(s,1H,NH).
Workup
- washwashed successively with water, 0.5N hydrochloric acid solution, and brine
- dry with materialThe organic extracts were dried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
- customThe crude product was purified by chromatography on silica gel using 10:1 chlorobutane/ethyl acetate mixture as eluent
Sources & evidence
- ORD record
- ord-11d55361f24242fdb56899436bd16639
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05631206
Reaction notes
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