1-Butanol → HCID 68839873, compound

HRID 1517407Notes

Reaction equation

HRID 1517407 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][CH3:6].Cl[C:9]1[N:10]=[C:11]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH:30]2[C:35](=[O:44])[NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[CH:38]=2)[C:12]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH:16]=[CH:15][C:13]=2[N:14]=1>O1CCCC1.O.CCCCCC.C(OCC)(=O)C>[CH2:3]([O:7][C:9]1[N:10]=[C:11]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH:30]2[C:35](=[O:44])[NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[CH:38]=2)[C:12]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH:16]=[CH:15][C:13]=2[N:14]=1)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 2631-ButanolHCID 24758Sodium hydrideHCID 86617308HCID 86617308, compound

Product 1

HCID 68839873HCID 68839873, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

28 mg (0.7 mmole) of 60% by weight NaH in mineral oil was suspended in dry tetrahydrofuran (5 ml) under a N2 atmosphere, followed by the addition of n-butanol (0.6 mmole). Then, 2-chloro-[(N-3-methyl-phenylcarbamoyl)-piperazin-1-yl]-6-(3,4-dimethoxyphenyl)-pyrido[3,2-d]pyrimidine (149 mg, 0.29 mmole) was added. The mixture was heated at reflux under N2 for 2.5 hours and then diluted with water. The crude product was extracted four times from the reaction mixture with ethyl acetate. The organic extracts were combined, dried over MgSO4 and evaporated to dryness under reduced pressure. Preparative thin layer chromatography on silica using a n-hexane/ethyl acetate 1:4 mixture as eluent afforded the pure title compound (148 mg, yield 93%) which was characterized by its mass spectrum as follows: MS (m/z): 557 ([M+H]+, 100).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under N2 for 2.5 hours
  3. extractionThe crude product was extracted four times from the reaction mixture with ethyl acetate
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-74e5339492ca4cf08c450b5d36c3cc88
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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