Dimethyl methoxymalonate → HCID 178493927, compound

Participants

Reaction Steps

In process (A), dimethyl methoxymalonate and 4-benzyloxybenzamidine hydrochloride are reacted to obtain 4,6-dihydroxy-5-methoxy-2-(4-benzyloxyphenyl)pyrimidine (1), which is then chlorinated with phosphorus oxychloride to obtain a dichloro derivative (2). The compound (2) is debenzylated by hydrogenation using palladium-on-carbon to obtain 5-methoxy-2-(4-hydroxyphenyl)pyrimidine (3), which is again protected with a benzyl group [(3)→(4)], followed by demethylation [(4)→(5)]. Compound (5) is reacted with an optically active 3-fluoroalkyl mesylate to obtain compound (6). After removing the benzyl protective group by hydrogenation with palladium-on-carbon [(6)→(7)], compound (7) is reacted with an optically active 3-fluoroalkyl mesylate to obtain compound (8).

Provenance & Evidence