4-[1,1-Dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrile → 2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile

HRID 1073949Notes

Reaction equation

HRID 1073949 reaction equation
[CH3:1][C:2]([CH3:20])([O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[C:3]#[C:4][C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1>C1C(Cl)=CC=C(Cl)C=1>[CH3:1][C:2]1([CH3:20])[CH:3]=[C:4]([C:5]2[N:6]=[CH:7][CH:8]=[CH:9][N:10]=2)[C:19]2[CH:18]=[C:15]([C:16]#[N:17])[CH:14]=[CH:13][C:12]=2[O:11]1

Participants

3

Reactant 1

HCID 198955894-[1,1-Dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrile

Product 1

HCID 198956062,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrileYield 62.2%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

580 mg of 4-[1,1-dimethyl-3-(2-pyrimidinyl)-2-pro pynyloxy]benzonitrile were heated at reflux for 3 hours in 20 ml of dichlorobenzene. The solution was allowed to cool and was then evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:2) and subsequently ethyl acetate/petroleum ether (1:1) for the elution. There was obtained 361 mg of 2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile which melted at 108°-109.5° C. after recrystallization from tert-butyl methyl ether.

Workup

  1. temperatureto cool
  2. customwas then evaporated to dryness
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-bcf815e9b445493d94b48c35e55eb05d
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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