2-Bromo-6-(bromomethyl)pyridine → 5-((6-Bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Participants

Reaction Steps

The title compound was prepared in a manner similar to PREPARATION x9 using 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 300 mg, 1.324 mmol) in DMSO (20 mL) followed by sodium tert-butoxide (153 mg, 1.588 mmol) and 2-bromo-6-(bromomethyl)pyridine (332 mg, 1.324 mmol). 1H NMR (400 MHz, DMSO-d6) δ 2.92-3.04 (m, 1H), 3.12-3.24 (m, 2H), 3.40-3.53 (m, 2H), 3.62-3.72 (m, 1H), 3.86-4.00 (m, 2H), 4.19-4.28 (m, 1H), 4.42-4.64 (m, 2H), 7.31 (s, 4H), 7.36-7.43 (m, 4H), 7.56 (s, 3H), 7.72 (d, J=7.83 Hz, 4H). ESI-MS m/z [M+H]+ calc'd for C15H15BrClN5O, 396.01. found 396.1.

Provenance & Evidence