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

HRID 361480

反応式

HRID 361480 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 215842333-Methyl-7-(methylpivaloyl)xanthine収率 90.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6d684acec1174f1daab1ed470cec0ee7
出典データセット
uspto-grants-1999_02
特許番号
US05866576

関連ノート

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