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

HRID 558566Notes

Reaction equation

HRID 558566 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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 670011225-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-7-carboxylic acid ethyl esterHCID 178467822HCID 178467822, compound

Product 1

HCID 670011522-[5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-propan-2-olYield 63,250.602%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

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

Sources & evidence

ORD record
ord-db88d5509ce34c039cc519da0103cb74
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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