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

HRID 225264Notes

Reaction equation

HRID 225264 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-2e0c48f276d2478581c796f80821424e
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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