Sodium Hydroxide → HCID 178433775, compound

HRID 510364Notes

Reaction equation

HRID 510364 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([CH3:24])[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[CH3:23])=[C:4]2[N:3]=1.[OH-:25].[Na+]>O1CCCC1>[Cl:1][C:2]1[NH:3][C:4]2[N:5]([N:9]=[C:10]([CH3:24])[C:11]=2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=2[CH3:23])[C:6](=[O:25])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86724866HCID 86724866, compound

Product 1

HCID 178433775HCID 178433775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 5,7-dichloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}pyrazolo[1,5-a]pyrimidine (1.30 g, 3.47 mmol) in tetrahydrofuran (25 ml) was added sodium hydroxide solution (3 mL, 17.37 mmol). The reaction mixture was stirred at 50° C. for 3 hours. Solvent was removed. The residue was dissolved with ethyl acetate (50 mL) and 5% HCl solution (20 mL). Organic layer was separated and dried. The crude material was purified on silica gel column (methanol/DCM, 0-10% gradient solvent system) to give the product. It was used for next step. (0.88 g, 68%); LC/MS: MS (ES+) m/e 356 (MH+).

Workup

  1. customSolvent was removed
  2. dissolutionThe residue was dissolved with ethyl acetate (50 mL) and 5% HCl solution (20 mL)
  3. customOrganic layer was separated
  4. customdried
  5. customThe crude material was purified on silica gel column (methanol/DCM, 0-10% gradient solvent system)
  6. customto give the product

Sources & evidence

ORD record
ord-182b34b4b431428d92472807de544156
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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