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

HRID 657097Notes

Reaction equation

HRID 657097 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]=1

Participants

4

Reactant 1

HCID 866283692-[bis(methyloxy)methyl]-4-chloro-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one

Product 1

HCID 675473522-[Bis(methyloxy)methyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-oneYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To crude 2-[bis(methyloxy)methyl]-4-chloro-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (presumed 6.78 mmol) dissolved in MeOH was added 10% Pd/C (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).

Workup

  1. filtrationThe Pd/C was filtered off
  2. concentrationthe solution concentrated under vacuum
  3. customThe crude residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-4161c09107d84fe5b8a0d7c23eb7fed7
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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