Phosphorus oxychloride → 4-chloro-N-(3,5-dimethylphenyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

2-(3,5-Dimethyl-phenylamino)-3H-pyrimidin-4-one (2.01 g, 9.34 mmol) was dissolved in POCl3 (8.70 ml, 93.4 mmol) and the mixture was heated to 100° C. in a round bottom flask equipped with a reflux condenser and a drying tube. After 5 hours the reaction was cooled to room temperature and concentrated in vacuo. The residue was quenched by the addition of sat NaHCO3 (aq) and was extracted 3× with DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (dissolved sample in DCM, eluted with 85:15 hexane/EtOAc) to afford 4-chloro-N-(3,5-dimethylphenyl)pyrimidin-2-amine (4-3).

Provenance & Evidence