2-Methoxyethanol → 2-Methoxyethyl-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 225295Notes

Reaction equation

HRID 225295 reaction equation
[Na].[F:2][C:3]([F:25])([F:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:15]3[N:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]3[N:13]=[CH:12][CH:11]=2)[CH:5]=1.[CH3:26][O:27]CCO>>[CH3:26][O:27][CH2:23][CH2:22][O:21][C:19]([C:18]1[CH:17]=[N:16][N:15]2[C:10]([C:6]3[CH:5]=[C:4]([C:3]([F:24])([F:2])[F:25])[CH:9]=[CH:8][CH:7]=3)=[CH:11][CH:12]=[N:13][C:14]=12)=[O:20]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 5360545SodiumHCID 111984377-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester

Product 1

HCID 867367312-Methoxyethyl-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Procedure

One hundred milligrams of metallic sodium is added to 50 ml. of 2-methoxyethanol and after it has dissolved, 3.35 g. of ethyl 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate is added and the mixture is refluxed for one hour. On cooling, the desired compound crystallizes from the solution and is removed by filtration. Recrystallization from methylene chloride-hexane affords the product as crystals, m.p. 111°-112° C.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. temperatureOn cooling
  3. customthe desired compound crystallizes from the solution
  4. customis removed by filtration
  5. customRecrystallization from methylene chloride-hexane

Sources & evidence

ORD record
ord-fea19720acfa4f6eb0c55b791c674c70
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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