Sodium hydride → HCID 21934688, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-acetylpiperazin-1-yl)pyrimidin-4-amine 4-4 (0.1 g, 0.45 mmol) was dissolved in dry TBF and then 1 equivalent of sodium hydride (0.036 g, 0.45 mmol) was added and this was stirred for 20 minutes at 25° C. then 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.065 g, 0.45 mmol) was added followed immediately by 1 more equivalent of sodium hydride. The reaction was then stirred at 100° C. for 3 hours. The reaction was cooled to 25° C. and methanol was added. This solution was loaded directly onto a silica column and eluted with DCM:MeOH:NH4OH (95:5:0.5). Fractions were combined and evaporated to yield the product, 4-5. Hi-Res MS: calc: 330.1132 found: 330.1137. 1H-NMR (DMSO): 8.33 ppm (s, 1H); 8.19 ppm (d, 1H); 6.34 ppm (d, 1H); 3.88 ppm (m, 2H); 3.80 ppm (m, 2H); 3.57 ppm (m, 4H); 2.07 ppm (s, 3H).

Provenance & Evidence