Sodium Bicarbonate → 3-(5-Isopropyl-2,6-dioxo-3-pyridin-4-ylmethyl-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzaldehyde

Participants

Reaction Steps

A mixture of 6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-1-pyridin-4-ylmethyl-1H-pyrimidine-2,4-dione (1.2 g, 2.83 mmol), p-toluenesulfonic acid monohydrate (538 mg, 2.83 mmol), and water (15 drops) in acetone (20 ml) was heated under reflux for 3 hr. After cooling to room temperature, excess sodium bicarbonate was added and the mixture was stirred for 1 hr. Then the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexane (9:1)) to afford 978 mg (91%) of 3-(5-Isopropyl-2,6-dioxo-3-pyridin-4-ylmethyl-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzaldehyde as a white solid. 1H NMR (200 MHz, CDCl3) δ 1.12 (6H, d, J=7.0 Hz), 2.40 (3H, s), 2.70 (1H, m), 4.92 (2H, s), 6.90 (1H, s), 7.08 (1H, s), 7.11 (1H, s), 7.14 (1H, s), 7.43 (1H, s), 8.50 (2H, d, J=6.2 Hz), 9.73 (1H, s), 9.91 (1H, s). 6.85-6.89 (3H, m), 7.09 (1H, s), 7.21-7.27 (2H, m), 7.40 (1H, s), 8.98 (1H, s), 9.89 (1H, s).

Provenance & Evidence