Dimethyl Sulfoxide → 3-Methyl-7-(methylpivaloyl)xanthine

HRID 1954094Notes

Reaction equation

HRID 1954094 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].[H-].[Na+].CS(C)=O.Cl[CH2:20][CH2:21][C:22]([CH3:27])([CH3:26])[C:23]([O-])=[O:24]>O>[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([C:23](=[O:24])[C:22]([CH3:27])([CH3:26])[CH2:21][CH3:20])[C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 706393-MethylxanthineHCID 217530474-Chloro-2,2-dimethylbutanoate

Product 1

HCID 215842333-Methyl-7-(methylpivaloyl)xanthineYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This example illustrates a synthesis of 3-Methyl-7-methylpivaloyl-1-(8,9-oxidononyl)xanthine (inventive compound no. 1409). A mixture of 3-methylxanthine (Aldrich, 1.00 g, 6.0 mmol), sodium hydride (145 mg, 6.0 mmol) and dimethyl sulfoxide (20 mL) was stirred until homogeneous (0.5 hours). Chloromethylpivalate (865 mL, 904 mg, 6.0 mmol) was added and the reaction stirred for 18 hours. The reaction mixture was poured into water (70 mL) and then extracted with 25% ethanol/dichloromethane (4×60 mL). The combined organic extracts were dried over sodium sulfate and evaporated under vacuum to a volume of 40 mL. This solution was cooled in icewater, whereupon a thick white precipitate was formed. The solid was filtered off under suction and dried under vacuum to yield 1.43 g (90% yield) 3-methyl-7-(methylpivaloyl)xanthine (inventive compound no. 1404).

Workup

  1. stirringthe reaction stirred for 18 hours
  2. extractionextracted with 25% ethanol/dichloromethane (4×60 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. customevaporated under vacuum to a volume of 40 mL
  5. temperatureThis solution was cooled in icewater, whereupon a thick white precipitate
  6. customwas formed
  7. filtrationThe solid was filtered off under suction
  8. customdried under vacuum

Sources & evidence

ORD record
ord-d4c1a514e5ef4cfcb353967c17b3aad1
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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