Sodium Iodide → 7-Benzyl-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amine

HRID 2219962ノート

反応式

HRID 2219962 の反応式
[I-].[Na+].I.[CH2:4]([N:11]1[CH2:20][CH2:19][C:18]2[C:17](Cl)=[N:16][C:15]([CH2:22][O:23][CH3:24])=[N:14][C:13]=2[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1>O1CCOCC1>[CH2:4]([N:11]1[CH2:20][CH2:19][C:18]2[C:17]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][CH:27]=3)=[N:16][C:15]([CH2:22][O:23][CH3:24])=[N:14][C:13]=2[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 99644-(Trifluoromethyl)anilineHCID 24841Hydrogen iodideHCID 590215757-Benzyl-4-chloro-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidine

生成物 1

HCID 120043937-Benzyl-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amine収率 54%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Sodium iodide (720 mg, 4.8 mmol) and hydriodic acid (2.0 mL, 47% aqueous solution) were added to the solution of 7-benzyl-4-chloro-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidine as prepared for Example 5.B. and (1.2 g, 4.0 mmol) and 4-aminobenzotrifluoride (1.3 g, 8 mmol) in dioxane (20 mL) and the reaction solution was stirred at 100° C. overnight. Solvent was removed in vacuo and the residue was dissolved in water. Solid sodium carbonate was added to the solution to a pH>7 then extracted by ethyl acetate. Ethyl acetate phase was washed by brine, and dried over sodium sulfate. Solvent was removed and the residue was purified by column chromatography to yield the product as a beige solid (910 mg, 54%).

後処理

  1. customas prepared for Example 5.B
  2. customSolvent was removed in vacuo
  3. dissolutionthe residue was dissolved in water
  4. additionSolid sodium carbonate was added to the solution to a pH>7
  5. extractionthen extracted by ethyl acetate
  6. washEthyl acetate phase was washed by brine
  7. dry with materialdried over sodium sulfate
  8. customSolvent was removed
  9. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-fb4e4c33e84d4c7181f6aebe4fcd1fce
出典データセット
uspto-grants-2008_08
特許番号
US07414131B2

反応ノート

読み込み中…