Ethyl Acetate → HCID 22257985, compound

HRID 567904Notes

Reaction equation

HRID 567904 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:20]2[C:28]3[C:27](=[O:29])[N:26]([CH3:30])[C:25](=[O:31])[N:24]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:23]=3[S:22][C:21]=2[CH2:36][C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[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:20]2[C:28]3[C:27](=[O:29])[N:26]([CH3:30])[C:25](=[O:31])[N:24]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:23]=3[S:22][C:21]=2[CH2:36][C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)=[O:6])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 22257963HCID 22257963, compound

Product 2

HCID 78922-MethylpentaneHCID 22257985HCID 22257985, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (0.12 g) was added to a solution of 5-[(3-hydroxyphenyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (Example 27, 0.20 g) in dichloromethane (5 ml). After 2 hours, ethyl acetate (50 ml) was added and the solution was washed with saturated sodium bisulfite solution (25 ml), then with saturated sodium hydrogen carbonate solution (25 ml), then with brine (25 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative normal-phase HPLC with dichloromethane:ethanol gradient elution then recrystallised from ethyl acetate:isohexane to give the title compound (0.05 g).

Workup

  1. washthe solution was washed with saturated sodium bisulfite solution (25 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by preparative normal-phase HPLC with dichloromethane
  6. washethanol gradient elution
  7. customthen recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-67aa6259f33e46caaf6d3b7909c00b46
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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