N-[5-(benzyloxy)pyrimidin-2-yl]hexanamide → N-(5-Hydroxypyrimidin-2-YL)hexanamide

HRID 906316Notes

Reaction equation

HRID 906316 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[N:11][C:12]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:13][CH:14]=1

Participants

4

Reactant 1

HCID 67391208N-[5-(benzyloxy)pyrimidin-2-yl]hexanamide

Product 1

HCID 58339660N-(5-Hydroxypyrimidin-2-YL)hexanamideYield 46,142.898%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[5-(Benzyloxy)pyrimidin-2-yl]hexanamide (87.1 g, 0.29 mmol) was dissolved in methanol (2.4 L), the solution was added with 10% palladium/carbon (20 g), and the mixture was stirred at room temperature for 3 hours under hydrogen atmosphere. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to obtain N-(5-hydroxypyrimidin-2-yl)hexanamide (28.0 g, 46%) as pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-2cc988c048fc44649cb21d015dd6667d
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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