反应详情

温度

100 °C

To a 10 mL vial was added 5-((6-bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x27, 75 mg, 0.189 mmol), K2CO3 (52.3 mg, 0.378 mmol), PdCl2(dppf) (13.83 mg, 0.019 mmol) and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.053 mL, 0.378 mmol) in dioxane (2 mL) and H2O (0.4 mL) to give an orange suspension. The reaction vial was sealed, heated to 100° C., and stirred overnight. The reaction mixture was then diluted with ethyl acetate and washed with aqueous saturated NH4Cl (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give crude product, which was loaded onto an ISCO® silica gel cartridge (4 g) and eluted using an ethyl acetatehexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow solid (36 mg, 57%). 1H NMR (400 MHz, DMSO-d6) δ 2.45 (s, 3 H), 2.92-3.05 (m, 1 H), 3.12-3.27 (m, 2 H), 3.40-3.52 (m, 2 H), 3.61-3.74 (m, 1 H), 3.85-4.00 (m, 2 H), 4.18-4.28 (m, 1 H), 4.35-4.58 (m, 2 H), 7.10-7.17 (m, 2 H), 7.30 (s, 1 H), 7.60-7.68 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C16H18ClN5O, 331.12; found 331.2.

1. customto give an orange suspension
2. customThe reaction
3. customvial was sealed
4. washwashed with aqueous saturated NH4Cl (3×10 mL)
5. dry with materialThe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give crude product, which
9. washeluted
10. customThe product was collected
11. concentrationconcentrated in vacuo