Dimethylacetamide → 6-[(4-Hydroxybenzyl)amino]-2-methylpyrimidine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

6-chloro-N-(4-methoxybenzyl)-2-methylpyrimidin-4-amine (500 mg, 01.90 mmol) from Step 1 from this example, palladium (II) trifluoroacetate (27.1 mg, 0.082 mmol), zinc dust (23.6 mg, 0.36 mmol), rac-2-(di-t-butylphosphino)-1,1-binaphthyl (66.5 mg, 0.17 mmol), zinc cyanide (125 mg, 1.1 mmol) was added dimethylacetamide (10 mL) in a flask (flame-dried) and evacuated and back-filled with N2 (3×). The reaction was heated to 95° C. for 30 min, cooled to room temperature. Water (20 mL) was added, extracted with ethyl acetate (20 mL), second wash with brine (20 mL). The organic phase was dried by magnesium sulfate and filtered through silica gel pad (1 inch deep), concentrated and purified by column chromatography through a 40 gram RediSep Rf™ silica gel cartridge eluting with 18% ethyl acetate/hexanes to give the title compounds as a pale yellow oil.

Provenance & Evidence