Ammonia acetate → 2,5,6-Trimethylthieno[2,3-d]pyrimidin-4-amine

HRID 44366

Reaktionsgleichung

Reaktionsgleichung von HRID 44366
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:11](O)(=O)[CH3:12].[NH3:15].C(OCC)(OCC)(OCC)C>>[CH3:11][C:12]1[N:8]=[C:7]([NH2:15])[C:6]2[C:5]([CH3:9])=[C:4]([CH3:10])[S:3][C:2]=2[N:1]=1

Komponenten

4

Edukt 3

HCID 12432Ammonia acetateHCID 66221Triethyl orthoacetateHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Produkt 1

HCID 252243412,5,6-Trimethylthieno[2,3-d]pyrimidin-4-amineAusbeute 60 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-amino-4,5-dimethylthiophene-3-carbonitrile (200 mg, 1.32 mmol), ammonia acetate (204 mg, 2.64 mmol), and triethyl orthoacetate (2.0 mL) was stirred in a sealed tube at 120° C. overnight. After the reaction mixture was cooling down to room temperature, the precipitate was collected by filtration, rinsed with EtOAc and dried in the air to give title compound (52 mg, 60%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ2.41 (s, 3H), 2.45 (s, 3H), 2.56 (s, 3H), 5.28 (bs, 2H). MS 194 (MH+).

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooling down to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. washrinsed with EtOAc
  4. customdried in the air

Quellen und Nachweise

ORD-Eintrag
ord-351ac407a6b3414eafc82a489c82274a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541421B2

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