Water → HCID 86598683, compound

HRID 2054312Notes

Reaction equation

HRID 2054312 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][N:15]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:18]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[N:17][C:16]=23)[CH:9]=[CH:8][N:7]=1)(=O)C.C[O-].[Na+].O>CO>[F:34][C:31]([F:32])([F:33])[C:28]1[CH:29]=[CH:30][C:25]([C:18]2[CH:19]=[C:20]([C:21]([F:22])([F:23])[F:24])[N:15]3[N:14]=[CH:13][C:12]([C:10]4[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[CH:11]=4)=[C:16]3[N:17]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86598684HCID 86598684, compound

Product 1

HCID 86598683HCID 86598683, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-[5-(4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-pyridin-2-ylmethyl acetate (0.16 g, 0.33 mmol) in MeOH (1 ml) was added at room temperature NaOMe (5.4M in MeOH, 0.2 ml). The reaction mixture was stirred for 17 h, poured into water (40 ml) and extracted with dichloromethane (3 times 40 ml). The combined organic layers were washed with brine (100 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate) to yield the title compound (112 mg, 78%) as an orange solid. MS (ISP) 439.3 [(M+H)+]; mp 2102° C.

Workup

  1. extractionextracted with dichloromethane (3 times 40 ml)
  2. washThe combined organic layers were washed with brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-9bdee01cd8f34524849a5b4d6dc5a65d
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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