Morpholine → HCID 86667797, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-methyl-1H-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine-2.4-dione (1.6 g, 4.20 mmol, 1 eq) 17, and PCl5 (10.5 g, 50 mmol, 12 eq) was added at rt POCl3 (33.5 mL, 357 mmol, 85 eq) under Ar(g). The reaction mixture was refluxed at 115° C. overnight. Once cooled down to rt, the mixture was poured dropwise very slowly onto stirred crushed ice over 2 h, then warmed up to rt for 1 h. The resulting aqueous was extracted with EtOAc (3×100 mL) and CH2Cl2 (4×100 mL). The combined organics were dried over MgSO4 and the solvent was removed in vacuo. To this residue in dry MeOH (50 mL) was added at rt morpholine (0.92 mL, 10.5 mmol, 2.5 eq) under Ar(g). The reaction mixture was stirred for 3 h, then the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:1-0:1) to yield the product as a pale brown solid (384 mg, 30%).

Provenance & Evidence