Sulfuric Acid → 4-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxaldehyde

HRID 1447875Notes

Reaction equation

HRID 1447875 reaction equation
[F:1][C:2]([F:21])([F:20])[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]#N)=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S(=O)(=O)(O)[OH:35]>O1CCCC1>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([CH:18]=[O:35])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 157125564-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 233298694-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0.01 mole sample of 4-(α,α,α-trifluoro-m-tolyl)-imidazo[1,5-a]pyrimidine-8-carbonitrile in tetrahydrofuran at -40° C. is reacted with diisobutyl aluminum hydride. To the mixture is added saturated aqueous ammonium chloride followed by dilute sulfuric acid. The mixture is extracted with methylene chloride and the extract washed with water and dried (MgSO4). The solvent is removed under reduced pressure to give the product of the example.

Workup

  1. extractionThe mixture is extracted with methylene chloride
  2. washthe extract washed with water
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed under reduced pressure
  5. customto give the product of the example

Sources & evidence

ORD record
ord-0b4d6ac76efe4736adfd9c87d8220c3b
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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