Thionyl Chloride → (R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine

HRID 1355387Notes

Reaction equation

HRID 1355387 reaction equation
C([O:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17](COCC)[C:16]([NH:25][CH2:26][CH2:27]O)=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12])(=O)C.S(Cl)([Cl:33])=O>>[OH:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([NH:25][CH2:26][CH2:27][Cl:33])=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 69153821(R)-1-(5-acetoxyhexyl)-7-ethoxymethyl-8-(2-hydroxyethylamino)-3-methylxanthine

Product 1

HCID 69154242(R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthineYield 69%

Procedure

A mixture of (R)-1-(5-acetoxyhexyl)-7-ethoxymethyl-8-(2-hydroxyethylamino)-3-methylxanthine (3.95 g, 9.3 mmol) and thionyl chloride (25 ml) was stirred at room temperature for 3 hours. After concentrating under reduced pressure to remove unreacted thionyl chloride, ethanol (100 ml) and a 1.0 M solution of hydrogen chloride in diethyl ether (10.0 ml) were added. After the mixture was stirred at 75-80° C. for 16 hours, concentrating under reduced pressure provided (R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine (2.2 g, 69% yield) as a white powder.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customto remove unreacted thionyl chloride, ethanol (100 ml)
  3. additiona 1.0 M solution of hydrogen chloride in diethyl ether (10.0 ml) were added
  4. stirringAfter the mixture was stirred at 75-80° C. for 16 hours
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-f5181a090f384022b8f290f75c919d33
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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