m-Chloroperbenzoic acid → N-(4-tert-Butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-methoxypyrido[3,4-d]pyrimidin-4-amine

HRID 2219961Notes

Reaction equation

HRID 2219961 reaction equation
C1C=C(Cl)C=C([C:8](OO)=[O:9])C=1.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:24]3[CH2:34][CH2:33][N:32]([C:35]4[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:31][C:25]=3[N:26]=[C:27](SC)[N:28]=2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C[O-].[Na+]>C(O)C>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:24]3[CH2:34][CH2:33][N:32]([C:35]4[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:31][C:25]=3[N:26]=[C:27]([O:9][CH3:8])[N:28]=2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 10942334Sodium MethoxideHCID 12004390N-(4-tert-Butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 12004391N-(4-tert-Butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-methoxypyrido[3,4-d]pyrimidin-4-amineYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

m-CPBA (148 mg, 0.6 mmol) was added to the solution of N-(4-tert-butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine from Example 28.C. (88 mg, 0.2 mmol) in ethanol (7 mL) and stirred at room temperature for 1 hr. Solid thus formed was filtered out and dried in vacuo (50 mg). This solid was suspended in methanol (5 mL) and sodium methoxide (9 mg, 0.165 mmol) was added and stirred at 60° C. overnight. Solvent was removed in vacuo and residue was dissolved in ethyl acetate, washed by water, sodium hydrosulfite aqueous solution, brine and dried over sodium sulfate. Purified by column to yield the product as a white solid (33 mg, 39%).

Workup

  1. customSolid thus formed
  2. filtrationwas filtered out
  3. customdried in vacuo (50 mg)
  4. customSolvent was removed in vacuo and residue
  5. dissolutionwas dissolved in ethyl acetate
  6. washwashed by water, sodium hydrosulfite aqueous solution, brine
  7. dry with materialdried over sodium sulfate
  8. customPurified by column

Sources & evidence

ORD record
ord-821080b30b3049759a34dae54ae14429
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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