HCID 70004538, compound → HCID 70003854, compound

HRID 580900Notes

Reaction equation

HRID 580900 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:7]2=[N:6][C:5]=1[CH3:17].[H][H]>CO.[Pd]>[OH:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH:14]([O:15][CH3:16])[C:7]2=[N:6][C:5]=1[CH3:17]

Participants

5

Reactant 2

HCID 70004538HCID 70004538, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70003854HCID 70003854, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate 10 (14 g) in methanol (250 ml) was hydrogenated at 50° C. with palladium on activated carbon (10%) (2 g) as a catalyst. After uptake of hydrogen (2 eq.), the catalyst was filtered off. The filtrate was evaporated and the residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 10 g (71%) of (±)-6,7,8,9-tetrahydro-3-(2-hydroxyethyl)-9-methoxy-2-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one (intermediate 11).

Workup

  1. customThe filtrate was evaporated
  2. customthe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8f108b0d82d044378763685264b997cb
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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