Triethylamine → 2-{4-Fluoro-alpha-[(2-methylquinazolin-5-yl)amino]-2-methoxybenzyl}-1,1,1-trifluoro-4-methylpentan-2-ol

HRID 2118079Notes

Reaction equation

HRID 2118079 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH:6]([C:19]([OH:28])([CH2:24][C:25]([CH3:27])=[CH2:26])[C:20]([F:23])([F:22])[F:21])[NH:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[N:11][C:12]([CH3:18])=[N:13]3)=[C:4]([O:31][CH3:32])[CH:3]=1.C(OCC)(=O)C.C(N(CC)CC)C>CO.[Pd].[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH:6]([C:19]([OH:28])([CH2:24][CH:25]([CH3:26])[CH3:27])[C:20]([F:22])([F:21])[F:23])[NH:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[N:11][C:12]([CH3:18])=[N:13]3)=[C:4]([O:31][CH3:32])[CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 179850612-{4-Fluoro-alpha-[(2-methylquinazolin-5-yl)amino]-2-methoxybenzyl}-1,1,1-trifluoro-4-methylpent-4-en-2-ol

Product 1

HCID 692084812-{4-Fluoro-alpha-[(2-methylquinazolin-5-yl)amino]-2-methoxybenzyl}-1,1,1-trifluoro-4-methylpentan-2-olYield 16.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

17 mg (0.04 mmol) of (rac.) 2-{4-fluoro-alpha-[(2-methylquinazolin-5-yl)amino]-2-methoxybenzyl}-1,1,1-trifluoro-4-methylpent-4-en-2-ol is shaken in 2 ml of methanol, 2 ml of ethyl acetate and 0.05 ml of triethylamine with 20 mg of palladium on carbon (10%) for 5 hours under hydrogen atmosphere. The reaction mixture is mixed with 200 mg of activated manganese dioxide and filtered through Celite after 10 minutes. It is concentrated by evaporation, and 3 mg of the desired product is obtained after preparative thin-layer chromatography on silica gel (cyclohexane/ethyl acetate 50%).

Workup

  1. filtrationfiltered through Celite after 10 minutes
  2. concentrationIt is concentrated by evaporation

Sources & evidence

ORD record
ord-4005c7a4df9140d988bc4f428533afff
Source dataset
uspto-grants-2008_10
Patent number
US07442794B2

Reaction notes

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