p-Toluenesulfonic acid monohydrate → 7-Oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde

HRID 2233218Notes

Reaction equation

HRID 2233218 reaction equation
C[O:2][CH:3](OC)[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.CC1C=CC(S(O)(=O)=O)=CC=1.O>O.CC(C)=O>[O:14]=[C:11]1[NH:10][C:8]2[N:9]=[C:4]([CH:3]=[O:2])[N:5]=[CH:6][C:7]=2[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 675473522-[Bis(methyloxy)methyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one

Product 1

HCID 594374057-Oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of 2-[bis(methyloxy)methyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (0.87 g, 3.91 mmol) in 1:1 H2O/acetone (10 mL) was added p-TsOH.H2O (0.074 g, 0.39 mmol) and the reaction was heated at reflux for 2 days. The reaction was not complete, so additional p-TsOH.H2O (0.20 g) was added and the solution was refluxed for an additional 1 day. After the disappearance of starting material, the solution was concentrated under vacuum to yield the desired product as a white solid and the crude material was used directly in the next step (1.023 g).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 2 days
  3. temperaturethe solution was refluxed for an additional 1 day
  4. concentrationAfter the disappearance of starting material, the solution was concentrated under vacuum

Sources & evidence

ORD record
ord-6f0bb01c45694efd8f8650a2558cc229
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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