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

HRID 1903719Notes

Reaction equation

HRID 1903719 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

5

Reactant 3

HCID 20466637HCID 20466637, compoundHCID 23665647Potassium tert-butoxideHCID 178420728HCID 178420728, compound

Product 1

HCID 204666382,3,5,8-Tetrahydroimidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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).

Workup

  1. temperatureThe mixture was then heated to 50° to 60° C. for 48 hours

Sources & evidence

ORD record
ord-5d80c96e6d92450c86f0011825c77b1a
Source dataset
uspto-grants-1984_03
Patent number
US04438118

Reaction notes

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