Ammonia → HCID 66953988, compound

Participants

Reaction Steps

9-Deazaadenine (73 mg, 547 μmol) was added to a solution of (S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-N-methyl-3-(methylthio)propan-1-amine (80 mg, 365 μmol) and formaldehyde (0.044 ml, 37% aq, 547 μmol) in a 1,4-dioxane (2 ml) and water (0.5 ml) mixture and the resulting suspension heated to 90 C (bath temp). After 1 h the reaction was cooled to ambient and 7N NH3 in MeOH (2.5 ml) was added and the resulting reaction left to stir for a further 1 h. The reaction was then concentrated in vacuo and the residue purified by flash chromatography on silica gel eluting with 10% 7N NH3 in MeOH/DCM=>20% 7N NH3 in MeOH/DCM to afford the title compound (110 mg, 83%) as a syrup. 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.46 (s, 1H), 3.91 (m, 2H), 3.57 (m, 2H), 2.71 (dd, J=13.2, 4.1 Hz, 1H), 2.49 (m, 2H), 2.32 (m, 1H), 2.26 (s, 3H), 2.04 (s, 3H), 1.94 (m, 1H), 1.31 (s, 3H), 1.25 (s, 3H).

Provenance & Evidence