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

HRID 482258ノート

反応式

HRID 482258 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 215842333-Methyl-7-(methylpivaloyl)xanthine収率 90%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c0b5bd0b04e8470b9dc18c6a16097b15
出典データセット
uspto-grants-1998_08
特許番号
US05795897

反応ノート

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