Hydrogen Peroxide → HCID 178467478, compound

HRID 630292Notes

Reaction equation

HRID 630292 reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][S:6][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[N:11]=1)=[CH2:2].B.C1C[O:25]CC1.OO.[OH-].[Na+]>C1COCC1.O>[OH:25][CH:1]([C:3]1[N:4]=[CH:5][S:6][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[N:11]=1)[CH3:2]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 178437803HCID 178437803, compound

Product 1

HCID 178467478HCID 178467478, compoundYield 2.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[(4-ethenyl-1,3-thiazol-5-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (see Example 167; 130 mg, 0.41 mmol) in anhydrous THF 5 mL was added borane-THF solution (1M in THF; 5.0 mL, 5.0 mmol). The mixture was stirred at room temperature for 24 hours. After cooling to 0° C., hydrogen peroxide (30%, 1.8 mL, 18 mmol) was added to the reaction mixture, followed by 10N NaOH (1.0 mL, 10 mmol). The reaction mixture was stirred for 1.5 hours, and water (25 mL) was added. The reaction mixture was extracted with ethyl acetate (3×25 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated to provide the crude product, which was purified by combiflash using 0 to 15% MeOH:CH2Cl2 to provide 2-({[4-(1-hydroxyethyl)-1,3-thiazol-5-yl]methyl}sulfanyl)-6-(trifluoromethyl)pyrimidin-4-ol (3.0 mg). 1H NMR (500 MHz, DMSO-d6): δ 1.41 (d, 3H), 4.77 (q, 2H), 5.06 (m, 1H), 6.55 (s, 1H), 8.85 (s, 1H); M+338.

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringThe reaction mixture was stirred for 1.5 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto provide the crude product, which
  8. customwas purified by combiflash

Sources & evidence

ORD record
ord-c7e0915c1b56463994e7058596363a02
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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