Chemical and Pharmaceutical Bulletin · 1976 · 12 citations · 0 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisPolycyclic HeterocyclesPyrimidine AnalogsPyrimidine AnaloguesPyrimidine Chemistry
Reactions of 4-alkylpyrimidines with formamide in the presence of phosphoryl chloride (called the modified Vilsmeier reaction) were described. 4-Methylpyrimidine derivatives (I, III) gave 4-pyrimidinylpyrimidines (II, IV) respectively but 4-methylenepyrimidine derivatives (V, VII) afforded 5-hydroxy-6-[4-(5-methylpyrimidinyl)]-2, 4-diaza-2-heptenal (VI) or bis (5, 6, 7, 8-tetrahydro-8-quinazolinylidenemethyl) amine (VIII) and 8-formylaminomethinyl-5, 6, 7, 8-tetrahydroquinazoline (IX).