Réaction #66617

Équation de réaction

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

Solvants

water

methanol

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc (3×50 mL)
2. 2
   LavageThe organic solution was washed with Brine
3. 3
   Séchagedried over MgSO4
4. 4
   FiltrationThe solution was filtered
5. 5
   Concentrationconcentrated
6. 6
   AutreThe residue was purified on one preparative TLC plate (20×40 cm)
7. 7
   Lavageeluting with EtOAc
8. 8
   AutreProduct recovered

Mode opératoire

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.

Source