Ethanol → HCID 66750477, compound

HRID 75453Notes

Reaction equation

HRID 75453 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:13]3[CH2:14][CH2:15][CH:9]2[CH2:10][O:11][CH2:12]3)[C:5]([Cl:16])=[C:4]([N:17]2[CH:22]3[CH2:23][CH2:24][CH:18]2[CH2:19][O:20][CH2:21]3)[N:3]=1.C(O)C.[NH2:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C1(C)C=CC=CC=1>[Cl:16][C:5]1[C:4]([N:17]2[CH:22]3[CH2:23][CH2:24][CH:18]2[CH2:19][O:20][CH2:21]3)=[N:3][C:2]([C:32]2[CH:33]=[CH:34][C:29]([NH2:28])=[CH:30][CH:31]=2)=[N:7][C:6]=1[N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][O:11][CH2:12]2

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 866659028,8'-(2,5-Dichloropyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane)

Product 1

HCID 66750477HCID 66750477, compoundYield 61.3%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 8,8′-(2,5-dichloropyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane) (1.0 g, 2.7 mmol) in 1:1 ethanol:toluene (10 mL) was added 4-aminophenylboronic acid pinacol ester (0.7 g, 3.2 mmol), 2.0M solution of sodium carbonate (1.2 mL) and tetrakis(triphenylphosphine) palladium (0) (0.3 g, 10 mol %). The reaction was refluxed under nitrogen overnight. The reaction was cooled and water was added (75 mL) and the mixture was extracted 3 times with ethyl acetate. The organics were separated and dried over magnesium sulfate, then filtered through Magnesol™ and concentrated in vacuo to an oil. The crude product was purified via silica gel column with hexanes/ethyl acetate to yield the title compound as a white solid (0.708 g). MS m/z=428 (M+H).

Workup

  1. temperatureThe reaction was refluxed under nitrogen overnight
  2. temperatureThe reaction was cooled
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. customThe organics were separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through Magnesol™
  7. concentrationconcentrated in vacuo to an oil
  8. customThe crude product was purified via silica gel column with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-adf75e6a89994eaba3622780c441058b
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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