Potassium Iodide → (+/-)-4-{3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]piperidin-1-yl}butanoic acid methyl ester

HRID 2189056ノート

反応式

HRID 2189056 の反応式
[Br:1][C:2]1[C:10]2[C:9]([O:11][CH:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)=[N:8][CH:7]=[N:6][C:5]=2[O:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:24][O:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29]Br.[I-].[K+].C(N(CC)C(C)C)(C)C>C1COCC1.ClCCl.O>[CH3:24][O:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29][N:14]1[CH2:15][CH2:16][CH2:17][CH:12]([O:11][C:9]2[C:10]3[C:2]([Br:1])=[C:3]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[O:4][C:5]=3[N:6]=[CH:7][N:8]=2)[CH2:13]1

参加物

8

反応物 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 107604Methyl 4-bromobutyrateHCID 58280221rac-5-Bromo-6-phenyl-4-(piperidin-3-yloxy)furo[2,3-d]pyrimidine

生成物 1

HCID 58280260(+/-)-4-{3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]piperidin-1-yl}butanoic acid methyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Heat a mixture of 550 mg (1.47 mmol) of rac-5-bromo-6-phenyl-4-(piperidin-3-yloxy)furo[2,3-d]-pyrimidine, 532 mg (2.94 mmol) of 4-bromobutyric acid methyl ester, 24.4 mg (0.147 mmol) of potassium iodide and 0.77 ml (4.41 mmol) of N,N-diisopropylethylamine in 1.5 ml of THF under reflux for 2 h. After cooling, dilute with dichloromethane and add to water. After phase separation, extract the aqueous phase with dichloromethane. Combine the organic phases, wash with satd. sodium hydrogencarbonate solution, dry over magnesium sulphate and concentrate under reduced pressure. From the residue, after purification by preparative RP-HPLC (eluent: acetonitrile/water), 780 mg of the target product are isolated, which are used without further purification.

後処理

  1. temperatureHeat
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. customAfter phase separation
  5. extractionextract the aqueous phase with dichloromethane
  6. washwash with satd
  7. dry with materialsodium hydrogencarbonate solution, dry over magnesium sulphate
  8. concentrationconcentrate under reduced pressure
  9. customFrom the residue, after purification by preparative RP-HPLC (eluent: acetonitrile/water), 780 mg of the target product
  10. customare isolated
  11. customwhich are used without further purification

出典と根拠

ORDレコード
ord-6b868b763b2a41bcb950ccf6fc4bf4c3
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

読み込み中…