1,2-Dimethoxyethane → 2-(1-Cyclopentylpiperidin-4-yloxy)-5-{4-(pyrrolidin-1-ylcarbonyl)phenyl}pyrimidine

HRID 1666546Notes

Reaction equation

HRID 1666546 reaction equation
COCCOC.C(=O)([O-])[O-].[Na+].[Na+].[CH:13]1([N:18]2[CH2:23][CH2:22][CH:21]([O:24][C:25]3[N:30]=[CH:29][C:28](Br)=[CH:27][N:26]=3)[CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.[N:32]1([C:37]([C:39]2[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=2)=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]1>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.O>[CH:13]1([N:18]2[CH2:23][CH2:22][CH:21]([O:24][C:25]3[N:30]=[CH:29][C:28]([C:42]4[CH:41]=[CH:40][C:39]([C:37]([N:32]5[CH2:33][CH2:34][CH2:35][CH2:36]5)=[O:38])=[CH:44][CH:43]=4)=[CH:27][N:26]=3)[CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2773571(4-(Pyrrolidine-1-carbonyl)phenyl)boronic acidHCID 231159615-Bromo-2-[(1-cyclopentylpiperidin-4-yl)oxy]pyrimidine

Product 1

HCID 111660672-(1-Cyclopentylpiperidin-4-yloxy)-5-{4-(pyrrolidin-1-ylcarbonyl)phenyl}pyrimidineYield 475.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1,2-dimethoxyethane (3.0 ml) and aqueous 2 N sodium carbonate solution (1.0 ml) were added to 2-(1-cyclopentylpiperidin-4-yloxy)-5-bromopyrimidine (176 mg, 0.54 mmol), and then 4-(pyrrolidin-1-ylcarbonyl)phenylboronic acid (142 mg, 0.065 mmol) and tetrakis(triphenylphosphine)palladium(0) (30 mg, 0.026 mmol) were added thereto and stirred in a nitrogen atmosphere at 80° C. for 20 hours. The reaction mixture was cooled to room temperature, and water was added to it and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-200, chloroform:methanol=10:1) to obtain the entitled compound (130 mg, 57%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (C-200, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2f320d522f624efe8201afaafb2a434a
Source dataset
uspto-grants-2011_10
Patent number
US08044070B2

Reaction notes

Loading…