HCID 20466637, compound → 2,3,5,8-Tetrahydroimidazo[1,2-a]pyrimidine

Reaction equation

ClC1C=CC=C(C)C=1[N:9]1[CH2:14][CH:13]=[CH:12][N:11]2[CH2:15][CH2:16][N:17]=[C:10]12.CC(C)([O-])C.[K+].N1CCN2C=CCNC=12>CS(C)=O>[N:17]1[CH2:16][CH2:15][N:11]2[CH2:12][CH:13]=[CH:14][NH:9][C:10]=12

Participants

Procedure

Six hundred twenty milligrams of 8-(2-chloro-6-methylphenyl)-2,3,7,8-tetrahydro-imidazo[1,2-a]pyrimidine were dissolved in 5 ml of dimethylsulfoxide, and 280 mg of potassium tert.butoxide were added to this solution, under stirring. The mixture was then heated to 50° to 60° C. for 48 hours. Subsequent to this time, some of the 2,3,7,8-tetrahydro-imidazo[1,2-a]pyrimidine added isomerized to form 2,3,5,8-tetrahydro-imidazo[1,2-a]pyrimidine. After the solvent was evaporated and the mixture of isomers was dissolved in dilute 1 N hydrochloric acid, as described in Examples 1 and 2, the isomers were separated by fractional extraction at increasing pH values (monitored by thin layer chromatography).