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

HRID 2237867
Notes
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Reaction equation

HRID 2237867 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 Ether
Solvent

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-21c123743a4b4c5eb8a8254c56ea6284
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07718661B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes