Methane → HCID 178525289, compound

Participants

Reaction Steps

2.8 g (4.1 mmol) 3-[4-[1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]phenyl}-2,3-dibromo-propionic acid ethyl ester (part a of this example) was added to 56 mL of 1M potassium t-butoxide in t-butanol (Aldrich) at room temperature. The mixture was stirred at room temperature for 2.5 hours, then 0.10 mL water was added. The solution was stirred for an additional hour then 1 g charcoal was added in 250 mL water. The mixture was stirred for 30 minutes then filtered. The filtrate was acidified with conc. hydrochloric acid (pH=1), then the resulting suspension was stirred for 15 minutes, filtered then washed with 3×50 mL water. The solid was dried under reduced pressure to give 1.63 g (81%) of title compound; 1H-NMR (DMSO-d6)δ: 8.15 (d, J=8.0 Hz, phenyl CH, 2H), 7.73 (d, J=8.0 Hz, phenyl CH, 2H), 3.87 (d, J=6.6 Hz, CH2N, 2H), 3.74 (d, J=6.8 Hz, CH2N, 2H), 1.88 (br s, c-hexyl CH, 1H), 1.4–1.8 (m, c-hexyl CH, CH2, 11H), 0.8–1.2 (m, c-hexyl CH2, 10 H); MS (ES−): 487 (M−1), 443 (M−1−CO2).

Provenance & Evidence