3,6-dibenzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione → 3-benzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

HRID 742965Notes

Reaction equation

HRID 742965 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH2:15][N:16](CC3C=CC=CC=3)[CH2:17][CH2:18][C:11]=2[NH:10][C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)(=O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH2:15][NH:16][CH2:17][CH2:18][C:11]=2[NH:10][C:9]1=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 99501573,6-dibenzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 194233353-benzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dioneYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 70 g of 3,6-dibenzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione in 1.5 1 of glacial acetic acid was debenzylated in the 6-position by hydrogenolysis on 10 g of 10% palladium/activated charcoal at 70° C. and a hydrogen pressure of 3.5 bar. After the catalyst had been filtered off, the filtrate was concentrated under reduced pressure, the residual oil was taken up with 500 ml of water and the pH was adjusted to 8 with conc. sodium carbonate solution, with stirring, to give 46 g of a white precipitate of 3-benzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione.

Workup

  1. filtrationAfter the catalyst had been filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b3c4075f4db47d691591e077a25b04b
Source dataset
uspto-grants-1996_09
Patent number
US05556854

Reaction notes

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