Diboron → 8-Methyl-4-(alpha,alpha,alpha-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine

HRID 225260Notes

Reaction equation

HRID 225260 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[CH:15]=[N: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[N:16]=[CH: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 233298734-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylic acid

Product 1

HCID 233298508-Methyl-4-(alpha,alpha,alpha-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.010 mole of 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylic acid in tetrahydrofuran is added dropwise to a 0.02 molar solution of diborane in tetrahydrofuran chilled in an ice bath. The mixture is allowed to warm to room temperature and stand overnight. The mixture is poured onto ice and extracted with methylene chloride. The methylene chloride extract is washed with water and dried (MgSO4). The solvent is removed under reduced pressure to give the product of the example.

Workup

  1. temperaturechilled in an ice bath
  2. additionThe mixture is poured onto ice
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washis washed with water
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed under reduced pressure
  8. customto give the product of the example

Sources & evidence

ORD record
ord-fbfd2545f514470185fbfa4aae467df2
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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