Methyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate → methyl 3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate

HRID 2219043Notes

Reaction equation

HRID 2219043 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][C:12]2=[N:11][C:10]=1[C:20]([O:22][CH3:23])=[O:21])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][C:12]2=[N:11][C:10]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 1

HCID 59771042Methyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 59771070methyl 3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Intermediate methyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2a]pyrimidine-2-carboxylate prepared in Step 2b was dissolved in MeOH and catalytic 10% Pd/C was added at room temperature. The mixture was stirred under H2 atmosphere for 3.5 hours. Filtration of the catalyst and evaporation of methanol gave a residue to which diethyl ether was added; filtration afforded methyl 3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate as a pale brown solid with the spectroscopical properties identical to the compound described in Step 5a.

Workup

  1. filtrationFiltration of the catalyst and evaporation of methanol
  2. customgave a residue to which diethyl ether
  3. additionwas added
  4. filtrationfiltration

Sources & evidence

ORD record
ord-c95457d2259744498897ff966b811f4b
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

Loading…