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

HRID 1654695Notes

Reaction equation

HRID 1654695 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-269d794e01b44c05aeb7f76d416cde36
Source dataset
uspto-grants-1995_04
Patent number
US05409934

Reaction notes

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