Lithium Hydroxide → HCID 15958181, compound

HRID 270959Notes

Reaction equation

HRID 270959 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:28])=[N:8][N:9]2[C:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:12]=[N:11][C:10]=12)=[O:5])C.[Li+].[OH-]>O1CCCC1>[CH:15]1([C:14]2[N:9]3[N:8]=[C:7]([CH3:28])[C:6]([C:4]([OH:5])=[O:3])=[C:10]3[N:11]=[CH:12][C:13]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 58825012HCID 58825012, compound

Product 1

HCID 15958181HCID 15958181, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 178 mg (0.46 mmol) of 7-cyclohexyl-6-(4-fluoro-phenyl)-2-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester in 9 mL of tetrahydrofuran was added 2.8 mL (2.8 mmol) of 1 M LiOH solution, and the mixture was heated at reflux for 15 h. Since analysis by TLC revealed that starting material was still present, 2.8 mL (2.8 mmol) of 1 M LiOH solution was added, and reflux was continued for 60 h. The reaction mixture was then cooled to rt, concentrated, diluted with water, acidified with 10% HCl solution to pH=2, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, and evaporated to give 156 mg (96% yield, 90% purity) of 7-cyclohexyl-6-(4-fluoro-phenyl)-2-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (515) as a beige solid as indicated by 1H NMR; LC-MS—calcd for C20H20FN3O2 [M++H]+: 354.15, found: 354.2.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 15 h
  3. temperaturereflux
  4. concentrationconcentrated
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-b27c14ec85a5461f825654879a5609be
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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