Dimethylamine → HCID 18009144, compound

Participants

Reaction Steps

To a solution of 4-{4-[2,3-epoxypropoxy]anilino}-6-(2,5-dichloroanilino)pyrimidine (Reference Example 9; 316 ma) in DMF (3 ml) was added potassium tert-butoxide (1M solution in tetrahydrofuran. 0.86 ml) at −35° C. and the solution stirred for 30 minutes. 4-Methoxybenzyl bromide (0.32 ml) was then added and the solution allowed to warm to ambient temperature over 2.5 hours. After stirring for 1 hour at ambient temperature, dimethylamine (2M in MeOH, 2 ml) was added and the reaction stirred for a further 18 hours. The solution was then poured into water and extracted with EtOAc. The organic extract was dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with DCM:MeOH:concentrated ammonia; 91:8:1 to give the title compound (220 mg, 49%) as a colourless oil. NMR: 2.19 (6H, s), 2.21-2.40 (2H, m), 3.68-3.92 (6H, m), 4.76 (1H, m), 4.95 (2H, brs), 5.38 (1H, s), 6.81 (4H, m), 7.19 (2H, m), 7.35 (3H, m), 7.42 (1H, dd), 7.61 (1H; d), 8.21 (1H, s), 8.83 (1H, s); m/z 568 (MH+).

Provenance & Evidence