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

HRID 971236Notes

Reaction equation

HRID 971236 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium iodide (720 mg, 4.8 mmol) and hydriodic acid (2.0 mL, 47% aqueous solution) were added to a mixture of 7-benzyl-4-chloro-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidine as prepared for Example 5.B. (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 and the mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with 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).

Workup

  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. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customSolvent was removed
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b54ac170c6df40da817bdb9f34b19c1d
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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