Potassium Carbonate → 5-(4-Chloro-phenyl)-3-ethynyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 268989Notes

Reaction equation

HRID 268989 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:21]#[C:22][Si](C)(C)C)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO.CC(OC)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:16])([F:15])[F:17])[N:11]3[N:18]=[CH:19][C:20]([C:21]#[CH:22])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 670009455-(4-Chloro-phenyl)-7-trifluoromethyl-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 866079955-(4-Chloro-phenyl)-3-ethynyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 45.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(4-Chloro-phenyl)-7-trifluoromethyl-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine (13.3 g, 34 mmol) in THF (60 mL) and MeOH (150 mL) at 0° C. was added K2CO3 (467 mg, 10 mol %) and the mixture was stirred at 0° C. for 6 h, diluted with TBME and ice water, separated, washed with brine, dried over Na2SO4, concentrated and purified by column chromatography (heptane/EtOAc 100:0-90:10), triturated in heptane, filtered and dried to give the title compound(5.0 g, 45%) as an orange crystalline solid. MS (ISP) 322.2 [(M+H)+] and 324.2 [(M+2+H)+]; mp 102-103° C.

Workup

  1. customseparated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography (heptane/EtOAc 100:0-90:10)
  6. customtriturated in heptane
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-e555da3ecbb74f4897166e20c6d8bf3d
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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