Reaction #66617

Reaction equation

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

Solvents

water

methanol

water

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (3×50 mL)
2. 2
   WashThe organic solution was washed with Brine
3. 3
   Dryingdried over MgSO4
4. 4
   FiltrationThe solution was filtered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified on one preparative TLC plate (20×40 cm)
7. 7
   Washeluting with EtOAc
8. 8
   OtherProduct recovered

Procedure

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