Hydrogen Peroxide → HCID 178461778, compound

HRID 219741Notes

Reaction equation

HRID 219741 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C@H:22]([CH3:33])[CH2:23][O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27](SC)[N:26]=3)[CH2:17][CH2:16]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].OO.C(=O)(O)[O-:37].[Na+]>C(O)(=O)C>[C:1]([C:5]1[N:6]=[C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C@H:22]([CH3:33])[CH2:23][O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([OH:37])[N:26]=3)[CH2:17][CH2:16]2)[CH:8]=[C:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 69026795HCID 69026795, compound

Product 1

HCID 178461778HCID 178461778, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1 g of (S)-2-tert-butyl-4-cyclobutyl-6-{4-[2-methyl-3-(2-methylsulfanyl-pyrimidin-4-yloxy)-propyl]-piperazin-1-yl}-pyrimidine (2.12 mmol) were dissolved in 10 ml of acetic acid. 2 g of aqueous hydrogen peroxide (17.6 mmol, 30% in water) were added at 0° C. The reaction mixture was stirred for 15 h at room temperature, poured onto water and the aqueous phase was adjusted to alkaline pH with saturated sodium bicarbonate solution. After extraction with ethyl acetate, the organic phase was dried over magnesium sulfate, filtered, and the solvent evaporated. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (2%). Fractions containing the product were combined, the solvent was evaporated, and the residue treated with acetonitril, filtered and dried to yield 0.36 g of the title compound as a white solid.

Workup

  1. additionpoured onto water
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe crude product was purified by chromatography on silica gel
  7. additionFractions containing the product
  8. customthe solvent was evaporated
  9. additionthe residue treated with acetonitril
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-aaf8d404d8ce47ac8dbec807eb372ebd
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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