Ethanol → HCID 136344414, compound

Participants

Reaction Conditions

Reaction Steps

A high pressure reaction vial was charged with 2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (50 mg, 175 μmol) and ethanol (460 μL). The reaction was treated with 1-(2-fluorophenyl)piperazine (63.1 mg, 55.3 μL, 350 μmol) and was sealed. The reaction was then heated to 100° C. where it stirred overnight. At this time, the reaction was allowed to cool to room temperature. It was then diluted with methylene chloride and methanol and concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 1-10% methylene chloride/methanol) afforded 2-(4-(2-fluorophenyl)piperazin-1-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one as a purple oil (31.5 mg, 40.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm −0.32-0.07 (m, 9H) 0.84 (t, J=8.01 Hz, 2H) 3.07 (br. s., 4H) 3.51 (t, J=8.01 Hz, 2H) 3.73 (br. s., 4H) 5.34 (s, 2H) 6.31 (d, J=3.52 Hz, 1H) 6.89 (d, J=3.52 Hz, 1H) 6.95-7.25 (m, 4H) 10.83-11.10 (m, 1H). LC-MS calcd. for C22H31FN5O2S [(M+H)+] 444, obsd. 444.1.

Provenance & Evidence