Diisopropylethylamine → Methyl 4-chlorothieno[2,3-d]pyrimidine-6-carboxylate

HRID 32515

Reaktionsgleichung

Reaktionsgleichung von HRID 32515
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([S:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:12]=1[CH:23]=O>C1(O)CCCCC1>[Cl:10][C:11]1[C:12]2[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[S:17][C:13]=2[N:14]=[CH:15][N:16]=1

Komponenten

4

Edukt 2

HCID 81531DiisopropylethylamineHCID 66367174Methyl [(6-chloro-5-formylpyrimidin-4-yl)thio]acetate2×

Produkt 1

HCID 17965841Methyl 4-chlorothieno[2,3-d]pyrimidine-6-carboxylateAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7966CyclohexanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

DIPEA (2.1 mL) was added to methyl [(6chloro-5-formylpyrimidin-4-yl)thio]acetate (intermediate 9) (2.9 g) in cyclohexanol (50 mL) under an inert atmosphere. The reaction mixture was heated at 120° C. for 90 minutes. The solvent was evaporated and the product purified by flash chromatography on silica eluting with hexane:diethyl ether (4:1) to afford the title compound as a pale yellow solid (1.45 g, 53%);

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe product purified by flash chromatography on silica eluting with hexane:diethyl ether (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-2d4c77ee1d8a4649a46509546955b256
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427616B2

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