m-Chloroperbenzoic acid → 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyrimidine 1-oxide

HRID 892580Notes

Reaction equation

HRID 892580 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH: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.ClC1C=CC=C(C(OO)=[O:29])C=1>ClCCl.C(OCC)C>[C:18]([C:15]1[CH:16]=[CH:17][C:4]2[O:3][C:2]([CH3:20])([CH3:1])[CH2:7][CH:6]([C:8]3[N:9]=[CH:10][CH:11]=[CH:12][N+:13]=3[O-:29])[C:5]=2[CH:14]=1)#[N:19]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 198956393,4-dihydro-2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 99257182-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyrimidine 1-oxideYield 9.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

242 mg of 3,4-dihydro-2,2-dimethyl-4-(2-pyrimidinyl)-2H-1-benzopyran-6-carbonitrile were dissolved in 5 ml of dichloromethane at room temperature and 450 mg of m-chloroperbenzoic acid were added. After stirring overnight the mixture was washed with sodium bisulphite solution and sodium bicarbonate solution. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/ethanol/formic acid (40:4:1) for the elution. The product was obtained in the form of an oil which was dissolved in diethyl ether and washed with sodium bicarbonate solution. The organic phase was dried over sodium sulphate and evaporated. The resulting oil was crystallized from t-butyl methyl ether to give 25 mg of 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyrimidine 1-oxide of melting point 98°-100° C.

Workup

  1. washwas washed with sodium bisulphite solution and sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customThe product was obtained in the form of an oil which
  7. washwashed with sodium bicarbonate solution
  8. dry with materialThe organic phase was dried over sodium sulphate
  9. customevaporated
  10. customThe resulting oil was crystallized from t-butyl methyl ether

Sources & evidence

ORD record
ord-a6d955d18df247ce907091160da36dbb
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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