Ammonia methanol → HCID 66953614, compound

Participants

Reaction Steps

The product from Example 2.4 (0.124 g, 0.305 mmol) was stirred in a solution of 7M NH3-MeOH (25 ml) for 24 h in a sealed tube at 135° C. (oil bath). After cooling to rt the solvent was evaporated and the residue chromatographed on silica gel (CH2Cl2-7M NH3 in MeOH, 98:2) to give (S)-1-((4-amino-5-(benzyloxymethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-3-(methylthio)propan-2-ol (0.085 g, 72%) as a colourless gum. 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.47 (s, 1H), 7.28 (m, 5H), 5.66 (s, 2H), 4.58 (s, 2H), 3.97 (d, J=13.8 Hz, 1H), 3.91-3.83 (m, 2H), 2.84 (dd, J=12.1, 3.5 Hz, 1H), 2.62 (dd, J=12.1, 8.4 Hz, 1H), 2.56 (d, J=6.4 Hz, 2H), 2.09 (s, 3H). 13C NMR (CD3OD) δ 152.8, 151.6, 149.4, 137.7, 133.5, 129.5, 129.3, 129.2, 116.0, 114.3, 78.6, 71.4, 70.3, 54.6, 43.3, 40.4, 16.2. +ESMS Found 388.1813 (M+H)+ C19H26N5O2S requires 388.1807.

Provenance & Evidence