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Paper | Regular issue | Vol 24, No. 4, 1986, pp.997-1006
Published online, 1st January, 1970
DOI: 10.3987/R-1986-04-0997
Synthesis of 3,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-ones

Anker Jørgensen*

*Department of Chemistry, Odense University, Campusvej 55 DK-5230 Odense M., Denmark


A series of 9 new 3-aryl-3,7-dihydro-2,5,6-trimethyl-7-phenylmethyl-4H-pyrrolo[2,3-d]pyrimidin-4-ones 2a-i were prepared in 44-66% yields by heating methyl 2-acetamido-4,5-dimethyl-1-phenylmethyl-1H-pyrrolo-3-carboxylate 1 in a mixture of phosphorus pentoxide, triethylamine hydrochloride and an appropriate aniline at 150°C for 25-45 min. Similar reactions of 1 with primary alkylamines can lead to formation of 7-phenylmethyl-2,5,6-trimethyl-pyrrolo[2,3-d][1,3]oxazin-4(7H)-one 3 and 3-alkyl-3,7-dihydro-2,5,6-trimethyl-7-phenylmethyl-4H-pyrrolo[2,3-d]pyrimidin-4-one 7.