Ammonium formate → 2-(4-((S)-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenol

HRID 2079323Notes

Reaction equation

HRID 2079323 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[N:17]=[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[N:15]=2)[C@@H:10]([CH:32]([CH3:34])[CH3:33])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:32]([C@H:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[C:14]1[C:23]2[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=2)[N:17]=[C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[N:15]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 1361215792-(4-((S)-4-benzyl-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenol

Product 1

HCID 1361214602-(4-((S)-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenolYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

20 mg of Pd/C was added to a round-bottom flask, and the flask was flushed with nitrogen followed by evacuation of the atmosphere under vacuum. To the flask was then added a solution of 2-(4-((S)-4-benzyl-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenol (200 mg, 0.44 mmol) in methanol, followed by the addition of ammonium formate (32 mg, 0.88 mmol). The reaction was refluxed overnight. The reaction was filtered through a bed of Celite to remove the catalyst. The solvent was evaporated to yield 2-(4-((S)-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenol (126 mg). LC/MS: m/z 363.5 (M+H)+ at 2.13 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe flask was flushed with nitrogen
  2. temperatureThe reaction was refluxed overnight
  3. filtrationThe reaction was filtered through a bed of Celite
  4. customto remove the catalyst
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b38fec3bfb6d406b8e4c07f16e068df0
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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