4-Toluenesulfonyl chloride → 2,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

HRID 645694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645694
[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][NH:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CN(C1C=CC=CN=1)C>C(Cl)Cl.C(OC(=O)C)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[C:6]=2[N:7]=1

Komponenten

7

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 529828092,4-Dichloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine

Produkt 1

HCID 582908522,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidineAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 2,4-dichloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.58 g, 2.86 mmol) in CH2Cl2 (6 mL) was added diisopropylethylamine (DIPEA) (0.56 mL, 3.14 mmol) and p-toluenesulfonyl chloride (TsCl) (0.57 g, 3.0 mmol), followed by dimethylaminopyridine (DMAP) (0.035 g, 0.286 mmol). After stirring at ambient temperature for 1 h, the solution was diluted with ethylacetate, and the organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine. The organic extract was then dried over Na2SO4 and concentrated to give a crude residue, which was purified by flash column (hexanes/ethyl acetate, 5:1) to yield 2,4-dichloro-5-methyl-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.38 g, 38%).

Aufarbeitung

  1. washthe organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine
  2. extractionThe organic extract
  3. dry with materialwas then dried over Na2SO4
  4. concentrationconcentrated
  5. customto give a crude residue, which
  6. customwas purified by flash column (hexanes/ethyl acetate, 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-356ec8cd4d0241ee91dabdd5ca5ab811
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705004B2

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