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

HRID 225261Notes

Reaction equation

HRID 225261 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 wth 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 wth 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-f8b2a515d358422c8a091134b9320aac
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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