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

HRID 657098Notes

Reaction equation

HRID 657098 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>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

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 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-carbaldehydeYield 147.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 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 (0.873 g, 3.91 mmol) in 1:1 H2O/acetone (10 mL) was added p-TsOH.H2O (0.074 g, 0.391 mmol) and the reaction was heated to 80° C. for 3 days with additional p-TsOH.H2O (0.20 g). After the disappearance of starting material, the solution was concentrated under vacuum to yield the desired product (1.023 g).

Workup

  1. concentrationAfter the disappearance of starting material, the solution was concentrated under vacuum

Sources & evidence

ORD record
ord-e21ec4b4e7b141b1b93c41537ae7fcca
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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