Acetic Acid → 2-Amino-4-chloro-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

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Reaction Conditions

Reaction Steps

Following the method of Bell et al. (J. Heterocyclic Chem. 1983, 20, 41), hydrogen chloride gas was bubbled for 2 minutes though a solution of 6.00 g (29.0 mmol) 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde oxime in 800 ml acetic acid at 115° C. The mixture was then stirred at 115° C. for 16 hours before being cooled to room temperature. The resulting crystals were removed by filtration, and the filtrate concentrated in vacuo. The residue was triturated in 100 ml ether to afford 4.60 g (93%) 2-amino-4-chloro-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 172 (M{37Cl}+, 23), 170 (M{35Cl}+, 71), 129 (53), 43 (100).

Provenance & Evidence