Morpholine → HCID 68515979, compound

Participants

Reaction Steps

To a solution of methyl 3-(6-formyl-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate (0.60 g) and titanium isopropoxide (1.10 ml) in methylene chloride (15 ml) was added morpholine (0.33 ml). The reaction was stirred at room temperature for 1 hour, then sodium triacetoxyborohydride (0.80 g) was added and stirred for a further 16 hours. The reaction mixture was diluted with water/methylene chloride (1:1) and filtered through diatomaceous earth (Celite®). The layers were separated, the aqueous layer extracted with methylene chloride. The combined organics were dried (magnesium sulphate) and concentrated to give a solid. The solid was purified by column chromatography on a silica column using initially methylene chloride and then a 19:1 mixture of methylene chloride and methanol as eluent to give methyl 4-methyl-3-[6-(morpholin-4-ylmethyl)-4-oxoquinazolin-3(4H)-yl]benzoate as a solid (0.62 g). NMR Spectrum: (DMSOd6) 2.18 (s, 3H), 2.40 (m, 4H), 3.59 (m, 4H), 3.63 (s, 2H), 3.87 (s, 3H), 7.62 (d, 1H), 7.75 (d, 1H), 7.85 (m, 1H), 8.03 (m, 2H), 8.12 (d, 1H), 8.28 (s, 1H); Mass Spectrum: M+H+ 394.

Provenance & Evidence