Sodium cyanoborohydride → (R)-N-((5-(benzyloxymethyl)-4-tert-butoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthio)ethanamine

Participants

Reaction Steps

A mixture of the product from Example 27.4 (0.130 g, 0.68 mmol), sodium cyanoborohydride (0.071 g, 1.13 mmol) and 5-(benzyloxymethyl)-4-tert-butyloxy-5H-pyrrolo[3,2-d]pyrimidin-7-carbaldehyde (0.192 g, 0.57 mmol) were evaporated from methanol (3×). The residue was dissolved in methanol (10 ml) and acetic acid added (5 drops). The reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was evaporated on to silica gel and chromatographed (methanol-triethylamine-DCM, 3:1:96) giving an orange oil (0.272 g, 93%). 1H NMR indicated that the product contained some (co-polar) starting amine. 1H NMR (CDCl3) δ 8.47 (s, 1H), 7.38 (s, 1H), 7.34-7.22 (m, 5H), 5.73 (s, 2H), 4.47 (s, 2H), 4.34 (q, J=6.8 Hz, 1H), 4.10 (Abq, 2H), 4.03 (m, 1H), 3.82 (m, 1H), 2.87 (q, J=5.7 Hz; 1H), 2.72 (dd, J=13.2, 5.7 Hz, 1H), 2.60 (dd, J=13.2, 6.0 Hz, 1H), 2.05 (s, 3H), 1.69 (s, 9H), 1.39 (s, 3H), 1.34 (s, 3H).

Provenance & Evidence