Hydrochloric Acid → (E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-acrylic acid

HRID 403484Notes

Reaction equation

HRID 403484 reaction equation
C[O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([CH2:24][CH3:25])=[N:15][N:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18][C:17]=23)=[CH:8][CH:7]=1.[Li+].[OH-].Cl>C1COCC1>[CH2:24]([C:14]1[C:13]([CH2:12][C:9]2[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[C:3]([OH:26])=[O:2])=[CH:11][CH:10]=2)=[C:17]2[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]2[N:15]=1)[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68379176(E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-acrylic acid methyl ester

Product 1

HCID 68378968(E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-acrylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-acrylic acid methyl ester (4) (2.94 g, 8.4 mmol) was dissolved in 25 ml of THF and 1M LiOH (25 ml) was added. The reaction mixture was stirred over night at rt. Then 0.5M HCl was added until a pH of 3.5 was reached. The mixture was extracted twice with EtOAc, the organic layer was washed with brine and dried over Na2 SO4. After evaporation the product was purified by recrystallisation from EtOAc to give a white solid.

Workup

  1. extractionThe mixture was extracted twice with EtOAc
  2. washthe organic layer was washed with brine
  3. customdried over Na2 SO4
  4. customAfter evaporation the product
  5. customwas purified by recrystallisation from EtOAc
  6. customto give a white solid

Sources & evidence

ORD record
ord-c6ca781fa186467abe9483d052a58f0e
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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