Ethyl Acetate → HCID 22257954, compound

HRID 567905Notes

Reaction equation

HRID 567905 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=C[CH:11]=1)[C:5](OO)=[O:6].[OH:12][C:13]1[CH:14]=[C:15]([S:19]([C:21]2[C:29]3[C:28](=[O:30])[N:27]([CH3:31])[C:26](=[O:32])[N:25]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:24]=3[S:23][C:22]=2[CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)=[O:20])[CH:16]=[CH:17][CH:18]=1.C(OCC)(=O)C>ClCCl>[CH3:11][CH2:2][CH2:3][CH:4]([CH3:9])[CH3:5].[OH:12][C:13]1[CH:14]=[C:15]([S:19]([C:21]2[C:29]3[C:28](=[O:30])[N:27]([CH3:31])[C:26](=[O:32])[N:25]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:24]=3[S:23][C:22]=2[CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)(=[O:6])=[O:20])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 22257985HCID 22257985, compound

Product 2

HCID 78922-MethylpentaneHCID 22257954HCID 22257954, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (50 mg) was added to a solution of 5-[(3-hydroxyphenyl)sulfinyl]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (Example 28, 80 mg) in dichloromethane (2 ml). After 2 hours, ethyl acetate (25 ml) was added and the solution was washed with saturated sodium bisulfite solution (10 ml), then with saturated sodium hydrogen carbonate solution (10 ml), then with brine (10 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate:isohexane to give the title compound (24 mg).

Workup

  1. washthe solution was washed with saturated sodium bisulfite solution (10 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-71ef97bf43f3447eb8fee7de7448945b
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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