Ethyl (2-chloroacetyl)carbamate → (7-Chloro-imidazo[1,2-c]pyrimidin-2-yl)-carbamic acid ethyl ester

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Reaction Conditions

Reaction Steps

A solution of 6-amino-4-chloropyrimidine (1) (0.504 g, 3.89 mmol) and N-chloroacetylurethane (0.770 g, 4.65 mmol) in 1,3-dimethyl-2-imidazolidinone (10 mL) was heated to 130° C. under nitrogen for 3 h. N-Chloroacetylurethane (0.770 g, 4.65 mmol) was added and the mixture was heated to 130° C. under nitrogen for a further 3.5 h. The black oily solution was poured onto ice (200 g) and the aqueous solution was extracted with ethyl acetate (3×250 mL). The organic fractions were combined, removal of solvent in vacuo gave an oily solid which was triturated with ether. Filtration of the solid and washing with ether gave urethane (2) (88 mg, 9%) as a solid. APCI-MS Found [M+H]+=241, 243.

Provenance & Evidence