Реакция #66617

Уравнение реакции

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

Растворители

water

methanol

water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with EtOAc (3×50 mL)
2. 2
   ПромывкаThe organic solution was washed with Brine
3. 3
   Сушкаdried over MgSO4
4. 4
   ФильтрацияThe solution was filtered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe residue was purified on one preparative TLC plate (20×40 cm)
7. 7
   Промывкаeluting with EtOAc
8. 8
   ДругоеProduct recovered

Методика

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.

Источник