3-benzyl-2-(1-hydroxyprop-2-enyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one → 3-benzyl-2-(1-hydroxypropyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1784475Notes

Reaction equation

HRID 1784475 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]2=[N:10][C:9]=1[CH:19]([OH:22])[CH:20]=[CH2:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]2=[N:10][C:9]=1[CH:19]([OH:22])[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 689099443-benzyl-2-(1-hydroxyprop-2-enyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 575931983-benzyl-2-(1-hydroxypropyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-oneYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.097 g (0.33 mmol) of the product from Step 7 (23) and 0.02 g of Palladium on activated carbon was stirred in 5 mL of ethyl acetate. The flask was equipped with a balloon containing hydrogen gas and the reaction mixture was stirred at ambient temperature for 3 days. The reaction mixture was then filtered through celite and washed with ethyl acetate. The resulting organic mixture was concentrated yielding 0.084 g (0.28 mmol, 85%) of 3-benzyl-2-(1-hydroxypropyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (24) as a clear oil.

Workup

  1. customThe flask was equipped with a balloon
  2. filtrationThe reaction mixture was then filtered through celite
  3. washwashed with ethyl acetate
  4. concentrationThe resulting organic mixture was concentrated

Sources & evidence

ORD record
ord-b09930744d88424abcededd998256f5f
Source dataset
uspto-grants-2009_03
Patent number
US07504405B2

Reaction notes

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