Water → 7-benzenesulfonyl-5-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1775177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1775177
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[NH:12][CH:11]=2)=[CH:5][N:4]=1.[H-].[Na+].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[C:21]1([S:27]([N:12]2[C:13]3[N:14]=[CH:15][N:16]=[CH:17][C:18]=3[C:10]([CH2:9][C:6]3[CH:5]=[N:4][C:3]([S:2][CH3:1])=[N:8][CH:7]=3)=[CH:11]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 579631715-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 579631247-benzenesulfonyl-5-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 5-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine (56, 1.20 g, 4.66 mmol) in 55.0 mL of N,N-dimethylformamide, sodium hydride (0.280 g, 7.00 mmol) was added. The reaction mixture was stirred at room temperature for 20 minutes, followed by addition of benzenesulfonyl chloride (40, 0.714 mL, 5.60 mmol). The reaction was stirred at room temperature for 3 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (57, 1.00 g).

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 20% ethyl acetate in hexane
  8. customthe solvents removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1d0c86ae85fb4229ad42cf522d63d4f2
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260437B2

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