Hydrogen Peroxide → HCID 86697956, compound

HRID 518788Notes

Reaction equation

HRID 518788 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[S:9][C:8]=2[C:18]([O:20][CH3:21])=[O:19])[CH:4]=[N:3]1.OO.C1([OH:30])C=CC=CC=1>C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:11]3[N:12]=[C:13]([S:16]([CH3:17])=[O:30])[N:14]=[CH:15][C:10]=3[S:9][C:8]=2[C:18]([O:20][CH3:21])=[O:19])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 996PhenolHCID 86697957HCID 86697957, compound

Product 1

HCID 86697956HCID 86697956, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

230 mg of methyl 7-(1-methyl-1H-pyrazol-4-yl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate, prepared by analogy with the method described in example 4, are added to a mixture of 25 equivalents of hydrogen peroxide (30% in water) and 1.49 g of phenol. The reaction medium is stirred for 30 minutes at ambient temperature and then heated at 50° C. for 1 hour. The reaction medium is diluted in ethyl acetate and washed with a saturated aqueous NaHCO3 solution and then with a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered, and then concentrated under vacuum so as to obtain the crude product, which is purified on silica, elution being carried out with a 0-10% gradient of methanol in dichloromethane so as to obtain 170 mg of methyl 7-(1-methyl-1H-pyrazol-4-yl)-2-(methylsulfinyl)thieno[3,2-d]pyrimidine-6-carboxylate in the form of a beige solid.

Workup

  1. temperatureheated at 50° C. for 1 hour
  2. washwashed with a saturated aqueous NaHCO3 solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum so as
  6. customto obtain the crude product, which
  7. customis purified on silica, elution

Sources & evidence

ORD record
ord-6795a2571e8a4b66926e6954d0e1359a
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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