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 657845Notes

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-yl]-benzoic acid methyl ester [(0.25 g, 0.92 mmol), WO2004060306, p134] 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-e6bfe3a2600b4ebe91c4826e37b1ed93
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076356B2

Reaction notes

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