3-(3-fluorophenyl)-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one → 3-(3-fluorophenyl)-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbaldehyde
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[N:12]3[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:11]3=[N:10][C:9]=2[CH2:20][OH:21])[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1.CCCCCC.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[N:12]3[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:11]3=[N:10][C:9]=2[CH:20]=[O:21])[CH:5]=[CH:6][CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of 3-(3-fluorophenyl)-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one (2.0005 g, 7.037 mmol, Prepared in Example 1) and manganese(IV) oxide (6.118 g, 70.37 mmol) in toluene (46.91 mL) was heated to reflux. After 3 h, the mixture was cooled to rt and filtered through a pad of Celite™. The pad was rinsed with DCM (200 mL). The filtrate was concd under reduced pressure to give an orange solid. The orange solid was suspended in hexane (50 mL), sonicated, and filtered to give 3-(3-fluorophenyl)-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbaldehyde as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (1 H, s), 7.78 (1 H, dd, J=8.6, 7.0 Hz), 7.18-7.68 (5 H, m), 7.06 (1 H, d, J=6.7 Hz), 2.92 (3 H, s); Mass Spectrum (ESI) m/e=283.0 (M+1).
Workup
- temperaturewas heated to reflux
- filtrationfiltered through a pad of Celite™
- washThe pad was rinsed with DCM (200 mL)
- customto give an orange solid
- customsonicated
- filtrationfiltered
Sources & evidence
- ORD record
- ord-ad900ded1a134172b5e5958e8207fcde
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754089B2
Reaction notes
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