Formaldehyde → HCID 66953959, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)-N-methylmethanamine (30 mg, 137 μmol) in dioxane (2 mL) and water (0.5 mL) was added 9-deazaadenine (27.5 mg, 205 μmol) and 37% aqueous formaldehyde (15.86 μl, 205 μmol). The reaction mixture was heated at 85° C. for 15 mins and then cooled and 7N NH3/MeOH (2.5 mL) was added. The solution was allowed to stand at RT for 3 days and concentrated to dryness. Chromatography (10% 7N NH3/MeOH in CH2Cl2) gave 7-(((((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methyl)(methyl)amino)methyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (34 mg, 93 μmol, 68% yield) as a syrup. 1H NMR (CD3OD) δ 8.16 (1H, s); 7.45 (1H, s); 3.86 (1H, dd, J=5.2, 11.9 Hz); 3.73-3.58 (3H, m); 3.52 (1H, dd, J=10.6, 11.7 Hz); 2.79 (1H, dd, J=2.5, 14.0 Hz); 2.53 (1H, dd, J=7.1, 14.0 Hz); 2.32 (1H, dd, J=5.5, 12.7 Hz); 2.24 (3H, s); 2.16 (1H, dd, J=8.1, 12.4 Hz); 2.06 (3H, s); 2.03-1.96 (1H, m); 1.36 (3H, s); 1.31 (3H. s). 13C NMR (CD3OD) δ 152.6, 151.4, 147.8, 130.6, 115.7, 113.4, 100.1, 75.9, 64.7, 57.3, 52.4, 43.6, 39.3, 38.3, 29.9, 20.4, 17.4.

Provenance & Evidence