Benzyl Bromide → 5-Benzyl-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

To 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 82 mg, 0.362 mmol) in DMF (2 mL) was added N,N-diisopropylethylamine (0.076 mL, 0.434 mmol) and (bromomethyl)benzene (0.047 mL, 0.398 mmol) to give a yellow solution, which was stirred at room temperature for 48 hours. The mixture was subsequently diluted with ethyl acetate and then washed with aqueous saturated NH4Cl (2×5 mL) and brine (2×5 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was loaded onto an ISCO® silica gel cartridge (4 g) and eluted using an ethyl acetate/hexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow solid (55 mg, 48%). 1H NMR (400 MHz, DMSO-d6) δ 2.91-3.10 (m, 2H), 3.10-3.22 (m, 1H), 3.32 (s, 1H), 3.40-3.54 (m, 1H), 3.60-3.75 (m, 1H), 3.81-4.01 (m, 2H), 4.15-4.30 (m, 1H), 4.41 (s, 2H), 7.20-7.42 (m, 6H). ESI-MS m/z [M+H]+ calc'd for C16H17ClN4O, 317.11. found 317.3.

1. customto give a yellow solution, which
2. washwashed with aqueous saturated NH4Cl (2×5 mL) and brine (2×5 mL)
3. dry with materialThe combined organic layers were dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. washeluted
7. customThe product was collected
8. concentrationconcentrated in vacuo

ORD record

ord-5813c78bcc0046d0be71eec34ea985ba

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791107B2