Réaction #302922

Équation de réaction

3-amino-1H-thieno[3,2-d]pyrimidine-2,4-dione

sodium nitrite

→

desired product

Rendement 49.2%

1H-Thieno[3,2-d]pyrimidine-2,4-dione

Rendement 49.2%

Solvants

acetic acid H2O

Conditions de réaction

Traitement

1. 1
   Autre(2 h)
2. 2
   AutreAcetic acid was removed under reduced pressure
3. 3
   Températurethe solution was cooled to 0° C
4. 4
   FiltrationThe resulting white solid was collected by filtration

Mode opératoire

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).

Source