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 38339노트

반응식

HRID 38339 반응식
[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

참가 물질

6

반응물 3

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

생성물 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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6f3ff7c1f99a4a2bbdc89dba3da0b66a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524725B2

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