Sulfuric Acid → HCID 67001152, compound

HRID 269003Notes

Reaction equation

HRID 269003 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 67001122HCID 67001122, compoundHCID 178467822HCID 178467822, compound

Product 1

HCID 67001152HCID 67001152, compoundYield 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]pyrimidine-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-4c4eadc63005461caac4368dfc04ad1c
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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