Dimethylamine → 5-iodo-N4-(6-methoxypyridin-3-yl)-N2,N2-dimethylpyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 2-chloro-5-iodo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (150 mg, 0.414 mmol), dimethylamine (2.0 M solution in tetrahydrofuran) (0.044 mL, 0.827 mmol) and ethanol (2 mL). The reaction mixture was stirred and heated in a Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 140° C. for 20 min. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 50% EtOAc/hexanes to give 5-iodo-N4-(6-methoxypyridin-3-yl)-N2,N2-dimethylpyrimidine-2,4-diamine (123 mg, 0.331 mmol, 80% yield). 1H NMR (300 MHz, CDCl3) δ 8.30 (s, 1H); 8.18 (s, 1H); 7.84 (dd, J=8.92, 2.48 Hz, 1H); 6.75 (d, J=8.92 Hz, 1H); 6.65 (s, 1H); 3.94 (s, 3H); 3.09 (s, 6H). m/z (ESI, +ve ion) 371.9 (M+H)+.

Provenance & Evidence