Methyl iodide → 5,6-Dimethyl-2-(methylthio)thieno[2,3-d]pyrimidin-4-amine

HRID 471494

Reaktionsgleichung

Reaktionsgleichung von HRID 471494
[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=1[NH:10][C:11]([NH:13]C(=O)C1C=CC=CC=1)=[S:12])#[N:2].[OH-].[Na+].[CH3:24]I>C(O)C>[CH3:8][C:7]1[C:3]2[C:1]([NH2:2])=[N:13][C:11]([S:12][CH3:24])=[N:10][C:4]=2[S:5][C:6]=1[CH3:9]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 899430N-benzoyl-N'-(3-cyano-4,5-dimethyl-2-thienyl)thiourea

Produkt 1

HCID 12123385,6-Dimethyl-2-(methylthio)thieno[2,3-d]pyrimidin-4-amineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamothioyl)-benzamide (Example 1a) (1.33 g, 4.22 mmol) in ethanol (25 mL) was added NaOH (2.0 N, 5.8 mL) at room temperature under nitrogen. After stirring at 100° C. under nitrogen for 0.5 h, the reaction mixture was cooled in an ice bath and MeI (0.8 mL) was added dropwise. After stirring for another 0.5 h, the resulting precipitate was collected by filtration, rinsed with water, 20% EtOH/H2O, and dried under vacuum to give the title compound (840 mg, 89%). 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 3H), 2.34 (s, 3H), 2.42 (s, 3H), 6.93 (bs, 2H). MS 226 (MH+).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. stirringAfter stirring for another 0.5 h
  3. filtrationthe resulting precipitate was collected by filtration
  4. washrinsed with water, 20% EtOH/H2O
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-80187deab81144d797a09a97593550db
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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