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

HRID 1654695
ノート
印刷プレビュー

反応式

HRID 1654695 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-269d794e01b44c05aeb7f76d416cde36
出典データセット
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05409934

反応ノート

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