4-(Methylsulfonyl)benzyl Bromide → (R)-2-chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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Reaction Steps

4-Methylsulphonylbenzyl bromide (121 mg, 0.485 mmol) was added to a mixture of (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x3, 100 mg, 0.441 mmol) and potassium tert-butoxide (59.4 mg, 0.529 mmol) in DMSO (2206 μL) at room temperature. The resultant mixture was stirred overnight at room temperature and subsequently diluted with EtOAc and water. The mixture was extracted twice with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, eluting with 0-10% MeOH/CHCl3 gradient) to afford the title compound as an off-white solid (55.9 mg, 32%). 1H NMR (400 MHz, DMSO-d6) δ 2.94-3.06 (m, 1 H), 3.08-3.29 (m, 5 H), 3.35-3.52 (m, 2 H), 3.67-3.76 (m, 1 H), 3.86-4.01 (m, 2 H), 4.25 (dd, J=13.64, 1.77 Hz, 1 H), 4.55 (s, 2 H), 7.30 (s, 1 H), 7.57 (d, J=8.34 Hz, 2 H), 7.87-7.92 (m, 2 H). ESI-MS m/z [M+H]+ calc'd for C17H19ClN4O3S, 395.09; found 395.2.

Provenance & Evidence