Synthetic Strategies toward the Synthesis of 2,4-Dimethoxypyrrolopyrimidine

Article abstract of DOI:10.1021/jo00155a026

Two approaches to prepare 2,4-dimethoxypyrrolo<3,2-d>pyrimidine (1) are described. 2,4-Dimethoxy-6-methyl-5-nitropyrimidine (2) was converted to 6-(cyanomethyl)-2,4-dimethoxy-5-nitropyrimidine (6) in two steps.Subsequent catalytic hydrogenation of 6 produced 1.In a second approach, 2 was formylated, giving rise to 6-<2-(dimethylamino)vinyl>-2,4-dimethoxy-5-nitropyrimidine (7).Hydrogenation of 7 resulted in the formation of 1.Reduction of 2 provided 5-amino-2,4-dimethoxy-6-methylpyrimidine (10).Reaction of compound 10 with triethyl orthoformate produced 2,4-dimethoxy-5-<(ethoxymethylene)amino>-6-methylpyrimidine (11).Reaction of 11 with lithium diisopropylamide gave 2,4-dimethoxy-5-isocyano-6-methylpyrimidine (12).