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

HRID 482258Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482258
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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c0b5bd0b04e8470b9dc18c6a16097b15
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795897

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