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Potassium tert-butoxide → 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-pyrimidine

HRID 1024865
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Reaktionsgleichung

Reaktionsgleichung von HRID 1024865
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[CH3:19][C:20]([CH3:23])([O-:22])[CH3:21].[K+]>C1COCC1.O>[Cl:8][C:6]1[CH:7]=[C:2]([O:22][C:20]([CH3:23])([CH3:21])[CH3:19])[N:3]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:5]=1
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Komponenten

5

Edukt 2

HCID 23665647Potassium tert-butoxide2×HCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Produkt 1

HCID 866198744-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step ii) (2 g) in THF (20 mL) was added potassium tert-butoxide (0.8 g) and the reaction mixture was stirred at ambient temperature for 20 h. Further potassium tert-butoxide (0.8 g) was added and the reaction mixture was stirred at ambient temperature for 4 h. The mixture was diluted with H2O and extracted with EtOAc (×3). The combined organic layers were washed with H2O and dried (MgSO4), filtered and evaporated. The resulting oil was purified by column chromatography on silica gel using MeOH/DCM (99:1 to 98:2 gradient) as eluent to give the subtitle compound as a clear, colourless oil. Yield: 0.68 g

Aufarbeitung

  1. stirringthe reaction mixture was stirred at ambient temperature for 4 h
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic layers were washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting oil was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-fc0fa91c77ed486094ff9dc2196f8e43
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722883B2

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