Acetic Acid → 6-benzyl-5-propyl[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 5-amino-1,3-thiazole4-carboxylate (prepared by the method of Golankiewicz and Januszczyk Tetrahedron 1985, 41, 5989-5994, 1 equiv), trimethyl orthobutyrate (2 equiv) and acetic acid (0.1 equiv) is heated at 90° C. for 3 h. Excess trimethyl orthobutyrate is removed by distillation. The residue is added to a solution of benzylamine (4.2 g, 40 mmol, 2 equiv) in ethanol (25 mL), and the resulting solution is heated at reflux for 18 h, then cooled and concentrated. The residue is triturated with EtOAc to provide 6-benzyl-5-propyl[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one (1-1).

Provenance & Evidence