Water → HCID 14182626, compound

HRID 1656347Notes

Reaction equation

HRID 1656347 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](=[O:7])[NH:3][CH:2]=1.CC(C)([O-])C.[K+].[C:14]([C:16]1[CH:17]=[CH:18][C:19]2[O:24][C:23]([CH3:26])([CH3:25])[CH:22]3[O:27][CH:21]3[C:20]=2[CH:28]=1)#[N:15].O>CS(C)=O.C(OCC)(=O)C>[C:14]([C:16]1[CH:17]=[CH:18][C:19]2[O:24][C:23]([CH3:26])([CH3:25])[C@@H:22]([OH:27])[C@H:21]([N:3]3[C:4](=[O:7])[CH:5]=[CH:6][N:1]=[CH:2]3)[C:20]=2[CH:28]=1)#[N:15]

Participants

7

Reactant 4

HCID 962WaterHCID 206954-HydroxypyrimidineHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 23665647Potassium tert-butoxide

Product 1

HCID 14182626HCID 14182626, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4(3H)-Pyrimidone (0.772 g, 8 mmol) was dissolved in dimethylsulphoxide (10 ml) and treated with potassium tert-butoxide (0.440 g, 4 mmol). The mixture was stirred for 30 minutes at ambient temperature and 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran (1.278 g, 6 mmol) added. The resulting mixture was heated at 90° C. for 30 minutes, cooled and poured into water. Extractive work up with ethyl acetate yielded a gum which was purified by chromatography on silica (ethyl acetate) to give trans-6-cyano-3,4-dihydro-2,2-dimethyl-4-(6(1H)-pyrimidinon-1-yl)-2H-1-benzopyran-3-ol 0.703 g, (38%), mpt 202°-3° (ethyl acetate/hexane).

Workup

  1. temperatureThe resulting mixture was heated at 90° C. for 30 minutes
  2. temperaturecooled
  3. customwas purified by chromatography on silica (ethyl acetate)

Sources & evidence

ORD record
ord-02be9ce378d24851a8d2368ba669085b
Source dataset
uspto-grants-1993_10
Patent number
US05254557

Reaction notes

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