methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate → (4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)methanol

HRID 1787737Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]([NH2:21])=[CH:19][C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])=[N:17]2)=[CH:12][CH:11]=1>O1CCCC1>[NH2:21][C:20]1[N:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=2)[N:17]=[C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (1M in tetrahydrofuran, 1.83 mL, 1.83 mmol) was added to an ice-cold solution of 4-[5-amino-3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-benzoic acid methyl ester [(0.25 g, 0.92 mmol), WO2004060306, p 134] in tetrahydrofuran (5 mL), and the mixture was stirred at 0° C. for 1 hour. The reaction was then quenched with water (0.35 mL) and 1M sodium hydroxide solution (0.35 mL) followed by further water (1 mL). The mixture was then extracted with diethyl ether, (10 mL) and the organic solution was dried over sodium sulfate and concentrated in vacuo to afford the title compound as red oil in 98% yield, 220.1 mg.

Workup

customThe reaction was then quenched with water (0.35 mL) and 1M sodium hydroxide solution (0.35 mL)
extractionThe mixture was then extracted with diethyl ether, (10 mL)
dry with materialthe organic solution was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-58885b6c3ef44a14a60079297aafa84d
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511057B2

Reaction notes

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