Acetic Anhydride → 2-Acetamido-4-methyl-6-benzyloxypyrimidine

Reaction equation

[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[C:1]([NH:8][C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1)(=[O:3])[CH3:2]

Participants

Procedure

Acetic anhydride (15.3 g, 0.15 mole) is added to a stirred suspension of 2-amino-4-methyl-6-benzyloxypyrimidine (23.6 g, 0.11 mole) in 150 ml of benzene. The mixture is heated at reflux for 4 hours. It is cooled, neutralized with aqueous sodium carbonate and the benzene layer separated. The benzene solution is concentrated under vacuum to an oil from which 2-acetamido-4-methyl-6-benzyloxy-pyrimidine melting at 121°-122° C. is isolated by crystallization from hexane n-butyl chloride.