2-[bis(methyloxy)methyl]-4-chloro-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one → 2-[Bis(methyloxy)methyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one
Reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[N:5]=[C:6](Cl)[C:7]2[CH2:13][CH2:12][C:11](=[O:14])[NH:10][C:8]=2[N:9]=1>CO.[Pd]>[CH3:17][O:16][CH:3]([O:2][CH3:1])[C:4]1[N:5]=[CH:6][C:7]2[CH2:13][CH2:12][C:11](=[O:14])[NH:10][C:8]=2[N:9]=1Participants
4
Procedure
To crude 2-[bis(methyloxy)methyl]-4-chloro-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (prepared from 1.43 g 4-chloro-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde) dissolved in MeOH (50 mL) was added 10% Pd/C (wet) (0.15 g). The solution was stirred under an atmosphere of H2 (balloon) overnight. The Pd/C was filtered off and the solution concentrated under vacuum. The crude residue was purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired product as a white solid (0.873 g, 58% over 2 steps).