Ammonium Hydroxide → HCID 58296335, compound

Participants

Reaction Steps

To a solution of 4-methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarboxylic acid (1.71 g, 5.90 mmole) in DMF (40 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyl uroniumhexafluoro phosphate (4.88 g, 12.8 mmol) and diisopropylethylamine (3.83 g, 29.6 mmol). The reaction mixture was stirred for 10 min before ammonium hydroxide (7.2 ml of 28%) was added. The mixture was stirred for additional 20 min and DMF was removed under vacuum. The residue was partitioned between ethyl acetate and water. The insoluble product was collected by filtration and dried under vacuum (0.54 g). The organic phase was separated, washed with 1N NaOH, water and dried over MgSO4. The solvent was removed under vacuum to give additional product (1.03 g) which was combined with the previously obtained precipitated product (1.27 g in total, 74% yield).

Provenance & Evidence