Sodium Hydroxide → HCID 66650561, compound

HRID 418163Notes

Reaction equation

HRID 418163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[N:14]=[CH:15][C:16]([C:17]([O:19]CC)=[O:18])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[N:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66650433HCID 66650433, compound

Product 1

HCID 66650561HCID 66650561, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.12 g, 0.4 mmol) and 0.5 N sodium hydroxide solution (4 mL) in methanol (4 mL) was heated to 70° C. for 2 h. The mixture was cooled, diluted with water (8 mL) and concentrated in vacuo. The aqueous solution was acidified to pH 2 by the addition of 3N HCl. The precipitate was isolated by filtration, washed with water, and dried to give 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.11 g, 100%). Off-white solid. MS (ISN) 272.3 [(M−H)−]; mp 309-311° C.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionThe aqueous solution was acidified to pH 2 by the addition of 3N HCl
  4. customThe precipitate was isolated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-94c4e313db5e46b596bb6446c5488c28
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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