Hydrochloric Acid → HCID 56646336, compound

HRID 1773600Notes

Reaction equation

HRID 1773600 reaction equation
Cl.C([SiH2][O:7][C:8](C)(C)[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:19]=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[N:23][C:22]=23)=[O:17])=[C:11]([O:27][CH3:28])[CH:10]=1)(C)(C)C.O.[OH-].[Na+]>ClCCl>[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:19]=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[N:23][C:22]=23)=[O:17])=[C:11]([O:27][CH3:28])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 131734711HCID 131734711, compound

Product 1

HCID 56646336HCID 56646336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of hydrochloric acid (1 M in Et2O, 3 mL) was added to a solution of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-phenyl]-amide (150 mg, 0.364 mmol) in dichloromethane (20 mL) and the resulting mixture was stirred at room temperature for 2 hours. Ice and water were then added and the pH of the mixture was neutralized by addition of an aqueous solution of sodium hydroxide (5%). The resulting mixture was extracted 3 times with dichloromethane. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography and by preparative TLC to give a yellow solid which was washed with water, methanol, dichloromethane, hexane and diethyl ether to give after drying pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (4-hydroxymethyl-2-methoxy-phenyl)-amide as a light yellow solid. MS=299 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted 3 times with dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography and by preparative TLC
  7. customto give a yellow solid which
  8. washwas washed with water, methanol, dichloromethane, hexane and diethyl ether
  9. customto give
  10. dry with materialafter drying pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (4-hydroxymethyl-2-methoxy-phenyl)-amide as a light yellow solid

Sources & evidence

ORD record
ord-323649b941a9490aa94b661d8145995a
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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