(5-Ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanone → 3-(5-Ethyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzaldehyde
Reaction equation
[CH2:1]([C:3]1[C:4]([C:13]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH2:22][OH:23])[CH:16]=2)=[O:14])=[N:5][C:6]([O:11][CH3:12])=[N:7][C:8]=1[O:9][CH3:10])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[C:4]([C:13]([C:15]2[CH:16]=[C:17]([CH:18]=[C:19]([CH3:21])[CH:20]=2)[CH:22]=[O:23])=[O:14])=[N:5][C:6]([O:11][CH3:12])=[N:7][C:8]=1[O:9][CH3:10])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of (5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanone (4.8 g, 15.2 mmol) and manganese dioxide (13.2 g, 152 mmol) in dichloromethane (110 ml) was stirred for 48 hr. at room temperature. The mixture was filtered through celite pad and the pad was washed with dichloromethane. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 3.22 g (67%) a white solid. m.p. 89-91° C.; 1H NMR (200 MHz, CDCl3) δ 1.07 (3H, t, J=7.4 Hz), 2.41-2.52 (5H, m), 3.92 (3H, s), 4.06 (3H, s), 7.91 (1H, s), 7.99 (1H, s), 8.10 (1H, s), 10.01 (1H, s).
Workup
- customat room temperature
- filtrationThe mixture was filtered through celite pad
- washthe pad was washed with dichloromethane
- customThe combined filtrate was evaporated in vacuo
- customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4))
Sources & evidence
- ORD record
- ord-5655953009694a26887cdddf2022cdcf
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106064B2
Reaction notes
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