Bromobenzene → HCID 50939680, compound

HRID 1468773Notes

Reaction equation

HRID 1468773 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1.Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(COC)OC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17]1

Participants

8

Reactant 4

HCID 7961BromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 67977685HCID 67977685, compound

Product 1

HCID 50939680HCID 50939680, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a round bottom flask, a mixture of 1-methyl-2-(piperidine-3-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (0.2 g, 0.70 mmol), bromobenzene (105 μl, 1.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (46 mg, 0.05 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (82 mg, 0.2 mmol) and potassium phosphate tribasic (0.43 g, 2.0 mmol) in dimethoxyethane (3 ml) was added at room temperature under nitrogen atmosphere and heated to 100° C. After stirring for 5 hours, the resulting mixture was cooled to room temperature. The resulting mixture was poured into water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=50/50) to afford 1-methyl-2-(1-phenyl-piperidin-3-yloxy)-1H-[4,4′]bipyrimidinyl-6-one as a yellow solid (67 mg, 0.18 mmol, 26%).

Workup

  1. additionwas added at room temperature under nitrogen atmosphere
  2. temperaturethe resulting mixture was cooled to room temperature
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-bca70c7af83043cd834081ca8fe5c391
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

Loading…