Triethylamine → HCID 20458237, compound

Participants

Reaction Steps

To a mixture of 4-benzyloxybutanamidine hydrochloride (14.6 g.) and triethylamine (33 g.) in EtOH (80 ml.) was added 2-chloroacrylonitrile (11.3 g.) and the solution was heated under reflux for 2 hours and then evaporated to dryness. The residue was partitioned between 10% aqueous HOAc (100 ml.) and EtOAc (200 ml.) and the EtOAc was reextracted with 10% v/v aqueous HOAc (2×100 ml.). The combined aqueous layers were basified with concentrated aqueous NaOH and extracted with EtOAc (3×75 ml.) and the EtOAc solution was washed with brine and dried to give 4-amino-2-(3-benzyloxypropyl)pyrimidine (9.8 g.). This amino-derivative was heated under reflux with 2,2,2-trifluoroethylisothiocyanate (10 g.) in acetonitrile (20 ml.) for 23 hours and the mixture evaporated to dryness. The residue was chromatographed on silica gel using CH2Cl2 containing 1% v/v MeOH as eluant to give 2-(3-benzyloxypropyl)-4-[3-(2,2,2-trifluoroethyl)thioureido]pyrimidine (10 g.).

Provenance & Evidence