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Water → 8-Amino-1,3-di(cylcopropylmethyl)-7-(isopropylsulphonyl)xanthine

HRID 1654695
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인쇄 미리보기

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HRID 1654695 반응식
[H-].[Na+].[NH2:3][C:4]1[NH:12][C:11]2[C:10](=[O:13])[N:9]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:8](=[O:18])[N:7]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[C:6]=2[N:5]=1.[CH:23]([S:26](Cl)(=[O:28])=[O:27])([CH3:25])[CH3:24].O>C(COC)OC.C(OCC)(=O)C>[NH2:3][C:4]1[N:12]([S:26]([CH:23]([CH3:25])[CH3:24])(=[O:28])=[O:27])[C:11]2[C:10](=[O:13])[N:9]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[C:8](=[O:18])[N:7]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[C:6]=2[N:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 71356CipamfyllineHCID 824082-Propanesulfonyl chloride

생성물 1

HCID 104524438-Amino-1,3-di(cylcopropylmethyl)-7-(isopropylsulphonyl)xanthine수율 45%

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane
용매
HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (0.35 g of a 60% suspension in oil, 8.7 mmol) was added to a suspension of 8-amino-1,3-di(cyclopropylmethyl)xanthine (2 g, 7.3 mmol ) in dimethoxyethane (40 ml) and the resulting mixture stirred at ambient temperature for 2 hr. Isopropylsulphonyl chloride (1.24 g, 8.7 mmol) was added and the mixture was heated at reflux for 18 hours. The reaction mixture was allowed to cool and then water (1 ml) was added dropwise. The mixture was added to ethyl acetate (200 ml), washed with water (50 ml) and dried (MgSO4). The solvent was removed at reduced pressure to afford the crude residue which was chromatographed on silica (acetone/hexane 1:3) to afford 8-amino-1,3-di(cylcopropylmethyl )-7-(isopropylsulphonyl)xanthine (1.25 g, 45%) as a yellow foam. Recrystallisation from ethyl acetate/hexane afforded a white flocculent solid, m.p. 119°-120° C.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureto cool
  4. washwashed with water (50 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed at reduced pressure
  7. customto afford the crude residue which
  8. customwas chromatographed on silica (acetone/hexane 1:3)

출처 및 근거

ORD 기록
ord-269d794e01b44c05aeb7f76d416cde36
출처 데이터셋
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05409934

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