Sodium Methoxide → HCID 12004389, compound

HRID 971231Notes

Reaction equation

HRID 971231 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 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium methoxide (16 mg, 0.3 mmol) was added to a 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 with water and brine and dried over sodium sulfate. After concentration, solid residue was triturated by diethyl ether to yield the product as a white powder (70 mg).

Workup

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

Sources & evidence

ORD record
ord-5bb17bb69a9645929df0db1bb21b45d6
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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