Sodium Nitrite → Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dione

HRID 215740

Reaktionsgleichung

Reaktionsgleichung von HRID 215740
N[N:2]1[C:7](=[O:8])[C:6]2[S:9][CH:10]=[CH:11][C:5]=2[NH:4][C:3]1=[O:12].N([O-])=O.[Na+]>C(O)(=O)C.O>[NH:4]1[C:5]2[CH:11]=[CH:10][S:9][C:6]=2[C:7](=[O:8])[NH:2][C:3]1=[O:12]

Komponenten

4

Edukt 2

HCID 23668193Sodium NitriteHCID 675407773-Aminothieno[3,2-D]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 7059273Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dioneAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-amino-1H-thieno[3,2-d]pyrimidine-2,4-dione (1.70 g, 9.3 mmol) in a 1:1 mixture of acetic acid/H2O (155 mL) was added sodium nitrite (1.92 g, 27.8 mmol) portion-wise. The reaction mixture was heated to 60° C. until the evolution of brown gas ceased (2 h). Acetic acid was removed under reduced pressure and the solution was cooled to 0° C. The resulting white solid was collected by filtration to afford 0.77 g of the desired product. MS: 167.3. 1H NMR (400 MHz, d6-N,N-dimethylsulfoxide (d6-DMSO)) δ ppm 11.40 (br s, 1H), 8.04 (d, J=5.2 Hz, 1H), 6.91 (d, J=5.3 Hz, 1H), 3.34 (br s, 1H).

Aufarbeitung

  1. custom(2 h)
  2. customAcetic acid was removed under reduced pressure
  3. temperaturethe solution was cooled to 0° C
  4. filtrationThe resulting white solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-8ab6e7187008492b843effe1877e865e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193178B2

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