Diisopropylethylamine → HCID 136247225, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-7-(2,3-dihydroxy-propyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (16 mg, 65.7 μmol) in ethanol (460 μL) was treated with 1-(2,6-difluorophenyl)piperazine trifluoroacetic acid salt (40.9 mg, 131 μmol) and N,N-diisopropylethylamine (36.6 μL, 210 μmol). The reaction was heated to 100° C., where it stirred overnight. At this time, the reaction was allowed to cool to room temperature. The reaction was then diluted with methylene chloride and methanol and concentrated in vacuo onto Celite®. Flash chromatography (4 g silica gel column, 1-4% methanol/methylene chloride) afforded 2-[4-(2,6-difluoro-phenyl)-piperazin-1-yl]-7-(2,3-dihydroxy-propyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a purple solid (15.3 mg, 57.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.17 (br. s., 4H) 3.23-3.31 (m, 2H) 3.54-3.70 (m, 4H) 3.71-3.93 (m, 2H) 4.09 (dd, J=13.68, 4.39 Hz, 1H) 4.67 (t, J=5.77 Hz, 1H) 4.94 (d, J=5.27 Hz, 1H) 6.24 (d, J=3.51 Hz, 1H) 6.80 (d, J=3.51 Hz, 1H) 6.95-7.24 (m, 3H) 10.85 (br. s., 1H). LC-MS calcd. for C19H22F2N5O3 [(M+H)+] 406, obsd. 406.0.

Provenance & Evidence