Electric Literature of 1303587-99-6,Some common heterocyclic compound, 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, molecular formula is C6H6ClN3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Synthesis of (2-chloro-6, 7-dihydro-8H-pyrimido [5, 4-b] [I, 4] omicronchialphazetaeta-8-yl) (phenyl) methanone [0426] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 0.87 mmol) in DMF (1.5 mL) under argon atmosphere were added sodium hydride (70 mg, 1.74 mmol) and benzoyl chloride (184 mg, 1.30 mmol) at 0C. The reaction mixture was stirred for 10 min at 0 C. After consumption of the starting materials (monitored by TLC), the reaction was quenched with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with a saturated sodium bicarbonate solution (20 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 35% EtOAc:hexanes to afford (2-chloro-6, 7- dihydro-8H-pyrimido [5, 4-b] [1, 4] oxazin-8-yl) (phenyl) methanone (160 mg, 66%>) as an off-white solid. 1H-NMR (CDC13, 500 MHz): delta 8.10 (s, 1H), 7.53-7.50 (m, 3H), 7.40-7.38 (m, 2H), 4.50-4.47 (m, 2H), 4.10-4.08 (m, 2H); LCMS: 276.3 (M+1); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.89 min. 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 50% EtOAc:hexanes (R 0.5).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, its application will become more common.
Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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