Methyl iodide → Methyl 5-((tert-butoxycarbonyl)(methyl)amino)pyrimidine-2-carboxylate

HRID 1526616

Reaktionsgleichung

Reaktionsgleichung von HRID 1526616
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:19])[C:9]1[CH:14]=[N:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 67980903Methyl 5-((tert-butoxycarbonyl)amino)pyrimidine-2-carboxylate

Produkt 1

HCID 90389408Methyl 5-((tert-butoxycarbonyl)(methyl)amino)pyrimidine-2-carboxylateAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 5-((tert-butoxycarbonyl)amino)pyrimidine-2-carboxylate (1.31 g, 5.16 mmol) in DMF (13 mL) was treated with cesium carbonate (2.19 g, 6.71 mmol) followed by iodomethane (0.64 mL, 10.32 mmol). The resulting suspension was stirred at ambient temperature for 5 h. The suspension was diluted with DCM (50 mL), filtered, concentrated, and purified by flash chromatography on silica gel eluting with a gradient of 0 to 40% EtOAc in DCM to give methyl 5-((tert-butoxycarbonyl)(methyl)amino)pyrimidine-2-carboxylate (1.16 g, 84% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.91 (s, 2H), 4.07 (s, 3H), 3.38 (s, 3H), 1.52 (s, 9H).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel eluting with a gradient of 0 to 40% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-c370875d86984e9d9572fbada6318bbb
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085576B2

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