Sodium hydride → 5-Bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine

HRID 2315

反応式

HRID 2315 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[Br:12].[H-].[Na+].Cl[C:16]1[N:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][N:17]=1>CN(C)C=O>[Br:12][C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=1[O:8][CH2:9][CH2:10][O:11][C:16]1[N:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][N:17]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 189311062-(6-Amino-5-bromopyrimidin-4-yloxy)ethanolHCID 219795322-Chloro-5-(methylthio)pyrimidine

生成物 1

HCID 196895255-Bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine収率 53.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(6-amino-5-bromopyrimidin-4-yloxy)ethanol (611 mg) in dimethylformamide (20 ml) is added sodium hydride (60% dispersion-type, 125 mg), and the mixture is stirred for 20 minutes. To the mixture is added 2-chloro-5-methylthiopyrimidine (461 mg), and the mixture is stirred at room temperature for three hours. To the mixture is added ice-water, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica get column chromatography (solvent; chloroform/methanol=20:1), and crystallized from ethyl acetate/diisopropyl ether to give 5-bromo-6-[2-(5-methythiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine (501 mg).

後処理

  1. stirringthe mixture is stirred at room temperature for three hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica
  8. customget column chromatography (solvent; chloroform/methanol=20:1)
  9. customcrystallized from ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-4bd91debc1224985b59b17dd05823067
出典データセット
uspto-grants-1998_03
特許番号
US05728706

関連ノート

読み込み中…