Potassium Carbonate → HCID 136389261, compound

HRID 1517417Notes

Reaction equation

HRID 1517417 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([CH:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[C:17]2[C:18]3[N:26]=[C:25](Cl)[CH:24]=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][C:31]=1[OH:45].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([CH:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[C:17]2[C:18]3[N:26]=[C:25]([C:34]4[CH:33]=[CH:32][C:31]([OH:45])=[C:30]([O:29][CH3:28])[CH:35]=4)[CH:24]=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 86617307HCID 86617307, compound

Product 1

HCID 136389261HCID 136389261, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[(N-3-chloro-phenylcarbamoyl)-piperazin-1-yl]-6-chloro-pyrido[3,2-d]pyrimidine (0.51 mmole) in 1,4-dioxane (15 ml) and water (5 ml) was added 2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (0.51 mmole), potassium carbonate (1.53 mmole) and tetrakis(triphenylphosphine)palladium(0) (0.02 mmole). The reaction mixture was refluxed for two hours, cooled down to room temperature and the solvents were evaporated in vacuo. The residue was purified by silica gel column chromatography (the mobile phase being an acetone/dichloromethane mixture in a ratio of 20:80), affording the title compound as a pure white powder (135 mg, yield 54%) which was characterized by its mass spectrum as follows: MS (m/z): 492 ([M+H]+, 100).

Workup

  1. temperatureThe reaction mixture was refluxed for two hours
  2. customthe solvents were evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (the mobile phase

Sources & evidence

ORD record
ord-b2ad0e5a12c4497ca36ed2ed6b5d8e71
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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