Hydrochloric Acid → 5,6-Dimethylthieno[2,3-d]pyrimidine-2,4-diamine

HRID 711634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711634
N[C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1C#N.[C:11]([NH:13][C:14]([NH2:16])=[NH:15])#[N:12].Cl.[OH-].[Na+]>O>[CH3:9][C:5]1[C:6]2[C:11]([NH2:12])=[N:13][C:14]([NH2:16])=[N:15][C:2]=2[S:3][C:4]=1[CH3:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrileHCID 178418324HCID 178418324, Verbindung

Produkt 1

HCID 126595335,6-Dimethylthieno[2,3-d]pyrimidine-2,4-diamineAusbeute 5,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-4,5-dimethylthiophene-3-carbonitrile (500 mg, 3.29 mmol), cyanoguanidine (276.6 mg, 3.29 mmol) and HCl (2 N, 1.5 mL) in water (10 mL) was refluxed under nitrogen for 2 h. The reaction mixture was cooled to room temperature, and basified with diluted NaOH aqueous solution to PH 7-8. After evaporation of water, the residue was purified by preparative HPLC eluting with acetonitrile and water to give the title compound (33 mg, 5%). 1H NMR (400 MHz, DMSO-d6) δ 2.22 (s, 3H), 2.27 (s, 3H), 5.85 (bs, 2H), 6.29 (bs, 2H). MS 195 (MH+).

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 2 h
  2. customAfter evaporation of water
  3. customthe residue was purified by preparative HPLC
  4. washeluting with acetonitrile and water

Quellen und Nachweise

ORD-Eintrag
ord-0da3ec8468ef4205bd6de2c8896a11fd
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181276B2

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