Aniline → HCID 86756051, compound
Reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[C:15]1([NH:14][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (15 g, 64.5 mmol) and aniline (12 mL, 132 mmol) in 200 mL of acetonitrile was stirred at room temperature for 24 hours. The mixture was then evaporated and ethyl acetate and 2M aqueous hydrochloric acid were added to the residue. The phases were separated and the organic phase was washed with aqueous hydrochloric acid, dried over sodium sulfate, filtered and evaporated. The resulting solid was purified by trituation with 1:3 ether/hexanes to give 14.2 g (64%) of ethyl 4-phenylamino-2-methylthio-pyrimidine-5-carboxylate as a white solid, mp 88.2-88.7° C.