Diboron → 3-Methyl-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine

HRID 1447876Notes

Reaction equation

HRID 1447876 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18](O)=O)=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.B#B>O1CCCC1>[CH3:18][C:17]1[CH:16]=[N:15][N:14]2[C:9]([C:5]3[CH:4]=[C:3]([C:2]([F:22])([F:1])[F:21])[CH:8]=[CH:7][CH:6]=3)=[CH:10][CH:11]=[N:12][C:13]=12

Participants

4

Reactant 2

HCID 6328200DiboronHCID 103353477-(alpha,alpha,alpha-Trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 233298353-Methyl-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.01 mole of 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid in tetrahydrofuran is added dropwise to a chilled (0° C.) solution of 0.02 mole of diborane in tetrahydrofuran. After standing overnight the mixture is poured onto ice and the product extracted into dichloromethane. The dichloromethane layer is washed with water, dried (MgSO4) and the solvent removed to give the product of the example.

Workup

  1. additionthe mixture is poured onto ice
  2. extractionthe product extracted into dichloromethane
  3. washThe dichloromethane layer is washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed
  6. customto give the product of the example

Sources & evidence

ORD record
ord-0ce4ee984eb843e694b0ffae2a5596be
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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