Sodium Methoxide → HCID 12004389, compound

HRID 2219957Notes

Reaction equation

HRID 2219957 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[C:6]([N:11]2[CH2:20][CH2:19][C:18]3[C:17]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[N:16][C:15](S(C)(=O)=O)=[N:14][C:13]=3[CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1>CO>[Cl:4][C:5]1[C:6]([N:11]2[CH2:20][CH2:19][C:18]3[C:17]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[N:16][C:15]([O:2][CH3:1])=[N:14][C:13]=3[CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12004367HCID 12004367, compound

Product 1

HCID 12004389HCID 12004389, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium methoxide (16 mg, 0.3 mmol) was added to the suspension of 7-(3-chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylsulfonyl)pyrido[3,4-d]pyrimidin-4-amine from Example 25 (100 mg, 0.2 mmol) in methanol (5 mL, anhydrous) and stirred at 60° C. overnight. Solvent was removed in vacuo, residue was dissolved in ethyl acetate and washed by water, brine, dried over sodium sulfate. After concentration, solid residue was triturated by diethyl ether to yield the product as a white powder (70 mg, 81%).

Workup

  1. customSolvent was removed in vacuo, residue
  2. dissolutionwas dissolved in ethyl acetate
  3. washwashed by water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration, solid residue
  6. customwas triturated by diethyl ether

Sources & evidence

ORD record
ord-b91f235afd244497bcebcf6db29aeba0
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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