Methanol → HCID 68920760, compound

HRID 1517408Notes

Reaction equation

HRID 1517408 reaction equation
[H-].[Na+].[CH3:3][OH:4].Cl[C:6]1[N:7]=[C:8]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH:27]2[C:32](=[O:41])[NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[CH:35]=2)[C:9]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)[CH:13]=[CH:12][C:10]=2[N:11]=1>O1CCCC1.O>[CH3:3][O:4][C:6]1[N:7]=[C:8]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH:27]2[C:32](=[O:41])[NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[CH:35]=2)[C:9]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)[CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 86617308HCID 86617308, compound

Product 1

HCID 68920760HCID 68920760, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

24 mg (0.6 mmole) of 60% by weight NaH in mineral oil was suspended in dry tetrahydrofuran (3 ml) under a N2 atmosphere followed by the addition of methanol (0.4 mmole). The mixture was stirred at room temperature for 15 minutes, and 2-chloro-4-[(N-3-methyl-phenylcarbamoyl)-piperazin-1-yl]-6-(3,4-dimethoxy phenyl)-pyrido[3,2-d]pyrimidine (104 mg, 0.2 mmole) was added. The solution was heated at reflux under N2 for 1 hour and diluted with water. The crude product was extracted from the reaction mixture with ethyl acetate and the organic layer was washed with brine, dried over MgSO4 and evaporated to dryness under reduced pressure. Preparative thin layer chromatography on silica, using a n-hexane/ethyl acetate mixture in a ratio of 1:5 as eluent, afforded the pure title compound (52 mg, yield 51%) which was characterized by its mass spectrum as follows: MS (m/z): 515 ([M+H]+, 100).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under N2 for 1 hour
  3. extractionThe crude product was extracted from the reaction mixture with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9dccb54a505a4500844cf76dbcd1207e
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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