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

HRID 2219962노트

반응식

HRID 2219962 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-fb4e4c33e84d4c7181f6aebe4fcd1fce
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414131B2

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