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

HRID 361480

반응식

HRID 361480 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

This example illustrates a synthesis of 1-(8,9-Oxidohexyl)-3-methyl-7-methylpivaloylxanthine (inventive compound no. 1410). 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 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).

후처리

  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. customformed
  7. filtrationThe solid was filtered off under suction
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-6d684acec1174f1daab1ed470cec0ee7
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866576

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