Ethyl isothiocyanatoformate → Ethyl (5-chlorothiazolo[5,4-d]pyrimidin-2-yl)carbamate

HRID 1875971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875971
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([NH2:17])=[CH:12][N:11]=1>CO>[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[N:17]=[C:7]([NH:6][C:4](=[O:5])[O:3][CH2:1][CH3:2])[S:8][C:14]=2[N:15]=1

Komponenten

4

Edukt 2

HCID 85320Ethyl isothiocyanatoformateHCID 2577975-Amino-2,4-dichloropyrimidine

Produkt 1

HCID 57476592Ethyl (5-chlorothiazolo[5,4-d]pyrimidin-2-yl)carbamateAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Ethoxycarbonyl isothiocyanate (4.32 mL, 36.6 mmol) and 2,4-dichloro-pyrimidin-5-ylamine (3.00 g, 18.29 mmol) were mixed neat and sonicated for 5 minutes to help dissolve. The mixture was stirred at ambient temperature for 10 minutes, at which time the entire mixture had solidified. Methanol (100 mL) was added and the mixture was refluxed for 30 minutes, cooled to ambient temperature and the solids were collected by filtration to afford ethyl 5-chlorothiazolo[5,4-d]pyrimidin-2-ylcarbamate (3.8 g, 80% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.64 (s, 1H) 9.05 (s, 1H) 4.31 (q, J=7.19 Hz, 2H) 1.32 (t, J=7.15 Hz, 3H).

Aufarbeitung

  1. customsonicated for 5 minutes
  2. dissolutionto help dissolve
  3. temperaturethe mixture was refluxed for 30 minutes
  4. temperaturecooled to ambient temperature
  5. filtrationthe solids were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-97a8884217814f86add29c88f61e6025
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309577B2

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