Water → 1-(5-Ketohexyl)-3-methylxanthine

HRID 482260Notes

Reaction equation

HRID 482260 reaction equation
CO.[Na].[O:4]=[C:5]([CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17](C(=O)C(C)(C)CC)[CH:16]=[N:15][C:14]=2[N:13]([CH3:28])[C:11]1=[O:12].O>CO>[O:4]=[C:5]([CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][CH:16]=[N:15][C:14]=2[N:13]([CH3:28])[C:11]1=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 190638701-(5-Oxohexyl)-3-methyl-7-(methylpivaloyl)xanthineHCID 86653488Methanol sodium

Product 1

HCID 150238981-(5-Ketohexyl)-3-methylxanthine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sodium methanol solution (prepared by adding sodium (20 mg, 0.9 mmol) to 1 ml of methanol) was added to a solution of 1-(5-oxohexyl)-3-methyl-7(methylpivaloyl)xanthine (270 mg, 0.7 mmol) in 4 ml of methanol and stirred for 15 min. The reaction mixture was poured into water (20 ml), then extracted with 25% ethanol/dichloromethane (4×50 ml). The organic extracts were combined, dried with sodium sulfate, and evaporated to give a yellow solid. The solid was washed with ether to remove impurities and give CT1505 (1-(5-oxohexyl)-3-methylxanthine) as a white solid (120 mg, 0.45 mmol, 65% yield).

Workup

  1. extractionextracted with 25% ethanol/dichloromethane (4×50 ml)
  2. dry with materialdried with sodium sulfate
  3. customevaporated
  4. customto give a yellow solid
  5. washThe solid was washed with ether
  6. customto remove impurities

Sources & evidence

ORD record
ord-6f593d16fd9440bea08cac18ff2406b3
Source dataset
uspto-grants-1998_08
Patent number
US05795897

Reaction notes

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