3-Hydroxymethyl-4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carboxylic acid benzyl ester → 2-[4-(2-Hydroxymethyl-piperazin-1-yl)-7-methyl-quinazolin-2-yl]-phenol

HRID 2079280Notes

Reaction equation

HRID 2079280 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:34])[N:18]=2)[CH:13]([CH2:35][OH:36])[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[OH:36][CH2:35][CH:13]1[CH2:12][NH:11][CH2:16][CH2:15][N:14]1[C:17]1[C:26]2[C:21](=[CH:22][C:23]([CH3:27])=[CH:24][CH:25]=2)[N:20]=[C:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[OH:34])[N:18]=1

Participants

4

Reactant 1

HCID 1361213213-Hydroxymethyl-4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 1361213512-[4-(2-Hydroxymethyl-piperazin-1-yl)-7-methyl-quinazolin-2-yl]-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 3-hydroxymethyl-4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carboxylic acid benzyl ester (200 mg, 0.41 mmol) in 1.7 mL of methanol was added 39 mg of Pd/C (10% wt Pd on carbon). The reaction mixture was stirred under a hydrogen atmosphere for 3 h. The mixture was filtered through Celite, and the solvent was removed to give 2-[4-(2-hydroxymethyl-piperazin-1-yl)-7-methyl-quinazolin-2-yl]-phenol. LCMS: m/z 351.2 (M+H)+ at 2.11 min (10%-99% CH3CN/H2O).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-df1d71cf669c41f3973cab350a102177
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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