Sodium Bicarbonate → 2-Methylsulfonyl-4-benzyloxy-pyrimidine

HRID 19667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19667
CS[C:3]1[N:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1.O[O:18][S:19]([O-:21])=O.[K+].[C:23]([O-])(O)=O.[Na+]>C1COCC1.CO.O>[CH3:23][S:19]([C:3]1[N:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1)(=[O:21])=[O:18]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 111838682-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidineHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 113575332-Methylsulfonyl-4-benzyloxy-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(methylthio)-4-[(phenylmethyl)oxy]pyrimidine (P9, 245 mg) in THF/MeOH 1/1 (15.6 mL) was added a solution of Oxone® (2.6 g) in water (14 mL). After 40 min a saturated NaHCO3 solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (10 g) eluting with dichloromethane/methanol from 100/0 to 99/1 to give the title compound as a white solid (230 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by a silica SPE cartridge (10 g)
  7. washeluting with dichloromethane/methanol from 100/0 to 99/1

Quellen und Nachweise

ORD-Eintrag
ord-6ed28fddb3784930a872ce9efc7b88b1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745458B2

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