Potassium Carbonate → 7-(5-Hydroxy-5-methyl-6-heptynyl)-3-methylxanthine

HRID 1738800Notes

Reaction equation

HRID 1738800 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].Cl[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:22])([CH3:21])[C:19]#[CH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:22][C:18]([CH3:21])([C:19]#[CH:20])[CH2:17][CH2:16][CH2:15][CH2:14][N:7]1[C:6]2[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 706393-MethylxanthineHCID 131980541-Chloro-5-hydroxy-5-methyl-6-heptyne

Product 1

HCID 218393427-(5-Hydroxy-5-methyl-6-heptynyl)-3-methylxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33.2 g (0.2 mol) of 3-methylxanthine in 350 ml of dimethylformamide were stirred with 32.1 g (0.2 mol) of 1-chloro-5-hydroxy-5-methyl-6-heptyne from Example 1B1) in the presence of 13.8 g (0.1 mol) of potassium carbonate at 120° C. for 6 hours. The hot mixture was then filtered, evaporated to dryness under reduced pressure and taken up in ethanol and, at the boiling point, diisopropyl ether was added to cloudiness, and the mixture was left to crystallize with cooling.

Workup

  1. filtrationThe hot mixture was then filtered
  2. customevaporated to dryness under reduced pressure
  3. additionwas added to cloudiness
  4. waitthe mixture was left
  5. customto crystallize
  6. temperaturewith cooling

Sources & evidence

ORD record
ord-e31cd4cb11704bedb52965070cc228db
Source dataset
uspto-grants-1999_10
Patent number
US05965555

Reaction notes

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