Sodium Hydroxide → 5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 900896Notes

Reaction equation

HRID 900896 reaction equation
C([C:3]1[C:21]([C:22]([OH:24])=[O:23])=[C:6]2[N:7]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:9]=[C:10]([CH:11]3[CH2:13][CH2:12]3)[N:5]2[N:4]=1)C.[OH-].[Na+]>CO.O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2[CH:9]=[C:10]([CH:11]3[CH2:13][CH2:12]3)[N:5]3[N:4]=[CH:3][C:21]([C:22]([OH:24])=[O:23])=[C:6]3[N:7]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66650894Ethyl 5-(4-chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 666504695-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 5-(4-chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.95 g, 2.8 mmol) and 2 N NaOH solution (5.6 mL) in MeOH (35 mL) was heated to 80° C. for 0.5 h. The mixture was cooled, diluted with water (150 mL) and washed with diethyl ether. The aqueous layer was acidified by the addition of 3N HCl to pH 2. The precipitate formed was isolated by filtration, washed with water, and dried to give the title compound (0.75 g, 86%). Off-white solid. MS (ISN) 312.3 [(M−H)−]; mp 256° C.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with diethyl ether
  3. additionThe aqueous layer was acidified by the addition of 3N HCl to pH 2
  4. customThe precipitate formed
  5. customwas isolated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-56cc9247804448e9a37d950338503655
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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