Sodium borohydride → [5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-methanol

HRID 269004Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:11]2[N:12]=[CH:13][CH:14]=[C:10]2[N:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:7]=1)=O)C.[BH4-].[Na+]>CO.O1CCCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]2[CH:7]=[C:6]([CH2:4][OH:3])[N:11]3[N:12]=[CH:13][CH:14]=[C:10]3[N:9]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-7-carboxylic acid ethyl ester (60 mg, 0.2 mmol) in MeOH/tetrahydrofuran (1:1 v/v, 1 mL) was added at 0° C. over 5 min sodium borohydride (75 mg, 2.0 mmol). The mixture was stirred at 0° C. for 1 h and then poured into ice-cold 3 N HCl (3 mL). The mixture was extracted with AcOEt and the organic layer was washed with H2O, dried (Na2SO4), and evaporated in vacuo. The residue was chromatographed on silica gel using AcOEt/cyclohexane (1:2 v/v) as eluent to give [5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-7-yl]-methanol (45 mg, 87%). Pale yellow solid. MS (ISN) 258.1 [(M−H)−]; mp 185-186° C.

Workup

extractionThe mixture was extracted with AcOEt
washthe organic layer was washed with H2O
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-d2bcd3e67b1c4cdf8dbbd6680fb8bf11
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446113B2

Reaction notes

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