Reacción #86526

Ecuación de reacción

sodium bicarbonate

6-bromo-7-(1-bromoethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

sodium azide

→

7-(1-azidoethyl)-6-bromo-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one

Rendimiento 97.5%

Disolventes

water

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 50 min
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 1 h
3. 3
   Otrothe solid precipitates
4. 4
   Filtraciónwere filtered off
5. 5
   LavadoThe solid was then washed with water (30 mL×3)
6. 6
   Otrodried

Procedimiento

To a suspension of 6-bromo-7-(1-bromoethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (6.85 g, 19.4 mmol) in N,N-dimethylformamide (30.1 mL) was added sodium azide (1.45 g, 22.4 mmol). The mixture slowly turned clear after 5-10 min. After 50 min, a solution of sodium bicarbonate (4.7 g, 56 mmol) in water (90 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 1 h and the solid precipitates were filtered off. The solid was then washed with water (30 mL×3), and dried to give 7-(1-azidoethyl)-6-bromo-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one as an off-white solid (5.94 g, 97.2%). LCMS calculated for C9H9BrN5OS (M+H)+: m/z 313.96, 315.96. Found: 313.75, 315.75. 1H NMR (400 MHz, DMSO-d6) δ 7.15 (q, J=1.3 Hz, 1H), 4.83 (q, J=6.8 Hz, 1H), 2.67 (d, J=1.4 Hz, 3H), 1.48 (d, J=6.8 Hz, 3H).

Fuente