Methyl Methanesulfonate → 2,4-dichloro-5-methyl-5H-pyrrolo(3,2-d)pyrimidine

HRID 334112

Reaktionsgleichung

Reaktionsgleichung von HRID 334112
[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12]OS(C)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[N:10]([CH3:12])[CH:9]=[CH:8][C:6]=2[N:7]=1

Komponenten

6

Edukt 3

HCID 4156Methyl MethanesulfonateHCID 10796Cesium carbonateHCID 53750532,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine

Produkt 1

HCID 147277632,4-dichloro-5-methyl-5H-pyrrolo(3,2-d)pyrimidineAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (2.67 g, 14.2 mmol), methanesulfonic acid methyl ester (1.26 mL, 14.9 mmol) and cesium carbonate (9.25 g, 28.4 mmol) in anhydrous N,N-dimethylformamide (21 mL) was stirred at RT (room temperature) under N2 for 15 h. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with 1:1 water/brine (3×) and brine (1×), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 2.50 g (87.1%) of 2,4-dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine as a white solid. MS(ESI) m/z: 202.2/204.1 [M+1]+.

Aufarbeitung

  1. washthe organic layer was washed with 1:1 water/brine (3×) and brine (1×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ad4ab2b30ba54eb98fe767b36759613a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883799B2

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