4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → Ethyl 4-methoxy-2-(methylthio)-pyrimidine-5-carboxylate

HRID 77462

Reaktionsgleichung

Reaktionsgleichung von HRID 77462
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH3:15][O-:16].[Na+]>CO>[CH3:15][O:16][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH3:15][O:16][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1

Komponenten

5

Edukt 2

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 10942334Sodium Methoxide

Produkt 2

HCID 12828997Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylateAusbeute 23 %HCID 20754788Ethyl 4-methoxy-2-(methylthio)-pyrimidine-5-carboxylateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (2.5 g, 10.74 mmol) and sodium methoxide (2.50 mL, 13.11 mmol) in methanol (107 mL) was stirred at room temperature under nitrogen for 4 h, quenched with acetic acid (5 mL), and concentrated. The oily residue was purified by flash chromatography on silica gel using 0-40% ethyl acetate in hexanes to give methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate as a white solid (0.52 g, 23%) and ethyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate as a colorless oil (0.61 g, 25%). Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.83 (s, 1H), 4.11 (s, 3H), 3.90 (s, 3H), 2.60 (s, 3H). LCMS: R.T.=0.92; [M+H]+=229.1. Ethyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate: 1H NMR (400 MHz, CHLOROFORM-d) δ 8.82 (s, 1H), 4.36 (q, J=7.0 Hz, 2H), 4.11 (s, 3H), 2.60 (s, 3H), 1.38 (t, J=7.2 Hz, 3H). LCMS: R.T.=0.92; [M+H]+=229.1.

Aufarbeitung

  1. customquenched with acetic acid (5 mL)
  2. concentrationconcentrated
  3. customThe oily residue was purified by flash chromatography on silica gel using 0-40% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-723c666ae8c8482e93f3065ff4335ef5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841301B2

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