Sulfuric Acid → 2-[5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-propan-2-ol

HRID 1293675Notes

Reaction equation

C(OC([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.[CH3:22][Mg]Br.C([O:27][CH2:28][CH3:29])C.S(=O)(=O)(O)O>C(OCC)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]2[CH:7]=[C:6]([C:28]([OH:27])([CH3:29])[CH3:22])[N:11]3[N:12]=[CH:13][CH:14]=[C:10]3[N:9]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-7-carboxylic acid ethyl ester (150 mg, 0.5 mmol) in diethyl ether (3 mL) was added at 0° C. 3 M methylmagnesium bromide/diethyl ether (0.37 mL, 1.1 mmol). The mixture was stirred at 20° C. for 2 h and then poured into 10% aqueous sulfuric acid. The mixture was extracted with AcOEt and the organic layer was washed with H2O, dried (Na2SO4) and evaporated in vacuo. The residue was triturated with cyclohexane to give 2-[5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-propan-2-ol (91 g, 63%). Off-white solid. MS (ISP) 288.1 [(M+H)+]; mp 113–115° C.

Workup

additionwas added at 0° C
extractionThe mixture was extracted with AcOEt
washthe organic layer was washed with H2O
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe residue was triturated with cyclohexane

Sources & evidence

ORD record: ord-bc8d884a9c56483f8517367250114cbe
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238808B2

Reaction notes

Loading…