2-Amino-4-[1-(3,4-dibenzyloxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl)pyrimidine → 2-Amino-4-[1-(3,4-dihydroxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl)pyrimidine

HRID 617188Notes

Reaction equation

HRID 617188 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:37])[C:15]3[CH:20]=[CH:19][C:18]([O:21]CC4C=CC=CC=4)=[C:17]([O:29]CC4C=CC=CC=4)[CH:16]=3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[N:3]=1>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:37])[C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([OH:29])[CH:16]=3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=2)[N:3]=1

Participants

5

Reactant 1

HCID 218515392-Amino-4-[1-(3,4-dibenzyloxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl)pyrimidine

Product 1

HCID 218515152-Amino-4-[1-(3,4-dihydroxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl)pyrimidineYield 74.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-[1-(3,4-dibenzyloxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl)pyrimidine (293 mg, 0.48 mmol) was dissolved in a mixture of methanol (3 ml) and ethyl acetate (3 ml), and hydrogenated under 1 atm in the presence of 10% palladium on carbon (80 mg) for about 3 hours. The catalyst was filtered off and washed with methanol. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (chloroform:methanol=97:3) to give the titled compound (155 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (chloroform:methanol=97:3)

Sources & evidence

ORD record
ord-39201b7659444ed097df6636f9b40586
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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