Ether hydrochloride → N*2*-(1,1-dioxo-hexahydro-1 lambda*6*-thiopyran-4-yl)-5-(2-isopropyl-4,5-dimethoxy-phenoxy)-pyrimidine-2,4-diamine HCl salt

HRID 38339Notes

Reaction equation

HRID 38339 reaction equation
[CH:1]([C:4]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:5]=1[O:6][C:7]1[C:8]([NH2:20])=[N:9][C:10]([NH:13][CH:14]2[CH2:19][CH2:18]S[CH2:16][CH2:15]2)=[N:11][CH:12]=1)([CH3:3])[CH3:2].O[O:30][S:31]([O-:33])=O.[K+].[ClH:35].CCOCC>CO.O>[ClH:35].[O:30]=[S:31]1(=[O:33])[CH2:18][CH2:19][CH:14]([NH:13][C:10]2[N:9]=[C:8]([NH2:20])[C:7]([O:6][C:5]3[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:4]=3[CH:1]([CH3:3])[CH3:2])=[CH:12][N:11]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 10953452Ether hydrochlorideHCID 23707502Potassium hydroxy sulfiteHCID 67333774HCID 67333774, compound

Product 1

HCID 86762022N*2*-(1,1-dioxo-hexahydro-1 lambda*6*-thiopyran-4-yl)-5-(2-isopropyl-4,5-dimethoxy-phenoxy)-pyrimidine-2,4-diamine HCl salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

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.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe organic solution was washed with Brine
  3. dry with materialdried over MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customThe residue was purified on one preparative TLC plate (20×40 cm)
  7. washeluting with EtOAc
  8. customProduct recovered

Sources & evidence

ORD record
ord-6f3ff7c1f99a4a2bbdc89dba3da0b66a
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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