1,3-Dibromopropane → 4-(4-((3-bromopropyl)amino)-6-methoxynaphthalen-2-yl)-N-methylpyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-amino-6-methoxy-2-naphthyl)-N-methylpyrimidin-2-amine (33), synthesized according to General Procedure B Steps 1-3 (1.00 g, 3.2 mmol) and acetonitrile (10 mL) was treated with N,N-diisopropylethylamine (1.2 mL, 7.1 mmol) followed by 1,3-dibromopropane (7.3 mL, 71.4 mmol). The resulting mixture was stirred at 65° C. for 10 h. The reaction mixture was partitioned between ethyl acetate (200 mL) and water (100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated (rotary). The crude compound was purified by column chromatography (silica gel) using 75% ethyl acetate/hexanes as the eluent to afford 4-(4-((3-bromopropyl)amino)-6-methoxynaphthalen-2-yl)-N-methylpyrimidin-2-amine (189) (0.55 g). LC/MS (m/z): 402 [M+H]

Provenance & Evidence