Sodium hydride → 3-Methyl-7-(methylpivaloyl)xanthine

HRID 482258Notes

Reaction equation

HRID 482258 reaction equation
O=C(C)CCCC[N:7]1[C:16](=[O:17])[C:15]2[NH:14][CH:13]=[N:12][C:11]=2[N:10]([CH3:18])[C:8]1=[O:9].CN1C2N=CNC=2C(=O)NC1=O.[H-].[Na+].Cl[CH2:35][CH2:36][C:37]([CH3:42])([CH3:41])[C:38]([O-])=[O:39]>CS(C)=O.O>[CH3:18][N:10]1[C:11]2[N:12]=[CH:13][N:14]([C:38](=[O:39])[C:37]([CH3:42])([CH3:41])[CH2:36][CH3:35])[C:15]=2[C:16](=[O:17])[NH:7][C:8]1=[O:9]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 706393-MethylxanthineHCID 150238981-(5-Ketohexyl)-3-methylxanthineHCID 217530474-Chloro-2,2-dimethylbutanoate

Product 1

HCID 215842333-Methyl-7-(methylpivaloyl)xanthineYield 90%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

This example illustrates a method for synthesis of CT1505 (1-(5-oxohexyl)-3-methylxanthine). A mixture of 3-methylxanthine (1.00 g, 6.0 mmol) and NaH (145 mg, 6.0 mmol) in DMSO (dimethyl sulfoxide) (20 ml) was stirred until homogeneous (about 30 min). Chloromethylpivalate (865 μl, 904 mg, 6.0 mmol) was added and the reaction mixture was stirred for 18 hrs. The reaction mixture was poured into 70 ml of water and extracted with 25% ethanol/dichloromethane (4×60 ml). The combined organic extracts were combined, dried with sodium sulfate, and then evaporated in a rotoevaporator to a volume of 40 ml. The solution was cooled in ice water and it formed a thick, white precipitate. The solid was filtered off under suction and dried under vacuum to give the 3-methyl-7-(methylpivaloyl)xanthine (1.43 g, 5.4 mmol, 90% yield).

Workup

  1. stirringthe reaction mixture was stirred for 18 hrs
  2. extractionextracted with 25% ethanol/dichloromethane (4×60 ml)
  3. dry with materialdried with sodium sulfate
  4. customevaporated in a rotoevaporator to a volume of 40 ml
  5. temperatureThe solution was cooled in ice water
  6. customit formed a thick, white precipitate
  7. filtrationThe solid was filtered off under suction
  8. customdried under vacuum

Sources & evidence

ORD record
ord-c0b5bd0b04e8470b9dc18c6a16097b15
Source dataset
uspto-grants-1998_08
Patent number
US05795897

Reaction notes

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