tert-Butanol → N,N-diethyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine

HRID 22787

Reaktionsgleichung

Reaktionsgleichung von HRID 22787
Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].[C:19](O)(C)(C)C.CCOC(C)=O>O.Cl>[CH2:14]([N:16]([CH2:17][CH3:18])[C:2]1[C:3]2[C:10]3[CH2:19][CH2:11][CH2:12][CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1)[CH3:15]

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 8021Diethylamine2×HCID 8857Ethyl AcetateHCID 78981712-Chloro-7-thia-9,11-diazatricyclo(6.4.0.0,2,6)dodeca-1(12),2(6),8,10-tetraene

Produkt 1

HCID 717848N,N-diethyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21885828Hydrate;hydrochlorideLösungsmittel

Versuchsvorschrift

To a slurry of 0.044 g 4-chloro-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine (0.196 mmol) in 1 mL of 100:1 H2O/HCl was added 0.014 g (0.02 mL, 0.106 mmol) diethylamine. The mixture was heated to reflux, and an additional 0.2 mL diethylamine and 1 mL of t-butanol were added and heated continued at reflux for an additional 1 h. TLC (20% EtOAc/80% pet ether) showed complete reaction and the 1H NMR of the isolated material was consistent with the desired product.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureat reflux for an additional 1 h
  5. customreaction

Quellen und Nachweise

ORD-Eintrag
ord-dcfb3b429c2544d6bb6f40646bccd630
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849638B2

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