Benzyl Bromide → 5-benzyl-2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Participants

Reaction Steps

The title compound was prepared in a manner similar to PREPARATION x38 using 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x1, 500 mg, 2.078 mmol), 1M lithium bis(trimethylsiylyamide) in hexanes (2.493 mL, 2.493 mmol) and (bromomethyl)benzene (0.271 mL, 2.286 mmol) in DMF (10 mL) at 0° C. for 18 hours. 1H NMR (400 MHz, DMSO-d6) δ 2.94-3.06 (m, 1H), 3.50-3.61 (m, 1H), 3.62-3.72 (m, 1H), 3.90-3.99 (m, 1H), 4.17-4.32 (m, 2H), 4.56-4.67 (m, 1H), 5.02-5.22 (m, 2H), 7.29 (s, 5H), 7.72 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C16H15ClN4O2, 331.09. found 331.2.

Provenance & Evidence