Reacción #66617

Ecuación de reacción

5-(2-isopropyl-4,5-dimethoxy-phenoxy)-N2-(tetrahydro-thiopyran-4-yl)-pyrimidine-2,4-diamine

OXONE

HCl ether

→

N2-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-5-(2-isopropyl-4,5-dimethoxy-phenoxy)-pyrimidine-2,4-diamine HCl salt

Disolventes

water

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc (3×50 mL)
2. 2
   LavadoThe organic solution was washed with Brine
3. 3
   Secadodried over MgSO4
4. 4
   FiltraciónThe solution was filtered
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified on one preparative TLC plate (20×40 cm)
7. 7
   Lavadoeluting with EtOAc
8. 8
   OtroProduct recovered

Procedimiento

To a mixture of 5-(2-isopropyl-4,5-dimethoxy-phenoxy)-N2-(tetrahydro-thiopyran-4-yl)-pyrimidine-2,4-diamine (0.19 g, 0.46 mmol) in 25 mL of methanol and 25 mL of water was added the OXONE (1.73 g, 1.4 mmol). This mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The organic solution was washed with Brine, dried over MgSO4. The solution was filtered and concentrated. The residue was purified on one preparative TLC plate (20×40 cm) eluting with EtOAc. Product recovered was stirred with 1.5 eq of 1M HCl/ether to afford 25 mg of N2-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-5-(2-isopropyl-4,5-dimethoxy-phenoxy)-pyrimidine-2,4-diamine HCl salt): MS (M+H); 441: MP; 255.1-257.8° C.

Fuente