2-chloro-11-Methyl-5H-benzo[e]pyriMido[5,4-b][1,4]diazepin-6(11H)-one synthesis
- Product Name:2-chloro-11-Methyl-5H-benzo[e]pyriMido[5,4-b][1,4]diazepin-6(11H)-one
- CAS Number:66427-86-9
- Molecular formula:C12H9ClN4O
- Molecular Weight:260.68
1234479-74-3
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Yield:66427-86-9 96%
Reaction Conditions:
with iron;acetic acid at 50; for 12 h;
Steps:
2-Chloro-11-methyl-5,11-dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one, (3)
A mixture of ethyl 2-((2-chloro-5-nitropyrimidin-4-yl)(methyl)amino)benzoate (2.1g, 6.2 mmol), ironpowder (3.9g, 69.8 mmol), and acetic acid (100 mL) was stirred vigorously at 50°C for 12 hours. Aftercooling, the reaction mixture was poured into water (600 mL). The solid was filtered, washed with water,and dried to give the title compound (1.5 g, 96%). 1H NMR (500 MHz, DMSO-d6) ppm 10.45 (s, 1 H)8.15 (s, 1 H) 7.73 (d, 1 H) 7.59 (m, 1 H) 7.28 (d, 1 H) 7.22 (m, 1 H), 3.34 (s, 3H). MS (m/z): 261.03[M+1]+.
References:
Chen, Bailing;Feru, Frederic;Feutrill, John;Gero, Thomas W.;Gray, Nathanael S.;Groendyke, Brian J.;Li, Bin;Li, Zhengnian;Pang, Kevin;Powell, Chelsea E.;Scott, David A.;Szabo, Hilary [Bioorganic and Medicinal Chemistry Letters,2020,vol. 30,# 4,art. no. 126948] Location in patent:supporting information
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