t-Butyl 4-hydroxy-7,8-dihydropyrido[4,3-d]pyriMidine-6(5H)-carboxylate synthesis

Yield:223609-09-4 70.4%

Reaction Conditions:

with sodium methoxide in methanol; for 6 h;Reflux;

Steps:

4.1.1.1. tert-butyl 4-hydroxy-7,8-dihydropyrido[4,3- d ]pyrimidine- 6(5 H )-carboxylate (2a)

A mixture of ethyl 1-methyl-4- oxopieridine-3-carboxylate (1.0 g, 3.70 mmol), formamidine acetate (0.46 g, 4.43 mmol) and sodium methoxide (0.80 g, 14.76 mmol) in anhydrous methanol (10 mL) was heated at reflux for 6 h. After completion of reaction as indicated by thin layer chro- matography (TLC), the mixture was concentrated immediately and then the resulting syrup was added purified water, treated with acetic acid to adjust pH to 6. The mixture was extracted with DCM (20 mL 3) and the organic layer was dried over anhydrous Na 2 SO 4 , filtered and concentrated to give compound 2a as a yellow solid (0.65 g, 70.4%); MS (ESI) m/z : 242.1 [M + H] + .

References:

Wu, Huinan;Lei, Hongrui;Tan, Zehui;Ma, Deyi;Li, Tong;Wang, Fuyi;Guo, Mengrao;Jiang, Nan;Zhai, Xin [Journal of Molecular Structure,2023,vol. 1271,art. no. 134108]