2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile → 3,4-dihydro-2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile

HRID 1073950Notes

Reaction equation

HRID 1073950 reaction equation
[CH3:1][C:2]1([CH3:20])[CH:7]=[C:6]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:4]=2[O:3]1>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:20])[CH2:7][CH:6]([C:8]2[N:9]=[CH:10][CH:11]=[CH:12][N:13]=2)[C:5]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 198956062,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 198956393,4-dihydro-2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrileYield 49.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.0 g of 2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile was dissolved in 100 ml of ethanol, added to 10% palladium-on-charcoal and shaken under an atmosphere of hydrogen at room temperature. After 2 hours the catalyst was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:1) for the elution. The product was recrystallized from cyclohexane to give 0.5 g of 3,4-dihydro-2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile of melting point 109°-111° C.

Workup

  1. filtrationAfter 2 hours the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution
  5. customThe product was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-e746f1275d8247138cb6775fcdba6add
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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