Hydrochloric Acid → 7-benzyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione

HRID 2200684노트

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HRID 2200684 반응식
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][O:21]C3CCCCO3)[C:13](=[O:28])[N:12](COCC[Si](C)(C)C)[C:11]=2[N:10]=[C:9]1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([O:44][C:45]([F:48])([F:47])[F:46])[CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:28])[NH:12][C:11]=2[N:10]=[C:9]1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([O:44][C:45]([F:46])([F:48])[F:47])[CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 904027997-benzyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(3-(trifluoromethoxy)phenoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione

생성물 1

HCID 904026367-benzyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione수율 123%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

To a solution of 7-benzyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(3-(trifluoromethoxy)phenoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (5.3 g, 7.68 mmol) in ethyl alcohol (20 mL) was added concentrated HCl (5 mL). The reaction was stirred at 80° C. overnight. The reaction was concentrated and the residue was neutralized with saturated sodium bicarbonate. This aqueous phase was extracted with ethyl acetate and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 7-benzyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (4.5 g, 100% yield) as white solid. 1H-NMR (DMSO-d6) δ 11.93(s, 1H), 7.62-7.57(t, 1H), 7.44-7.32(m, 8H), 5.42(s, 2H), 4.49-4.46(t, 1H), 3.89-3.86(t, 2H), 3.46-3.41(m, 2H), 1.72-1.65(m, 2H). LCMS retention time 2.560 min; LCMS MH+ 477.

후처리

  1. concentrationThe reaction was concentrated
  2. extractionThis aqueous phase was extracted with ethyl acetate
  3. customthe phases were separated
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ffaf4511cae94449847b19e38dff4138
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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