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Potassium Carbonate → HCID 58362383, compound

HRID 2361504
Notes
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Reaction equation

HRID 2361504 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=[C:4]2[N:3]=1.CC1(C)C(C)(C)OB([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])O1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.[Cu]I>[N:3]1[C:4]2[N:5]([C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH:6]=[CH:7][C:2]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2773231tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 583623562-Bromobenzo[4,5]imidazo[1,2-a]pyrimidine

Product 1

HCID 58362383HCID 58362383, compoundYield 44.8%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1,1′ Bis(diphenylphosphino)ferrocnee]dichloropalladium(II),w/DCM (0.033 g, 0.040 mmol) was added to a solution containing 2-bromobenzo[4,5]imidazo[1,2-a]pyrimidine (0.2 g, 0.806 mmol), tert-butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (0.386 g, 1.209 mmol), Copper(I) iodide (0.015 g, 0.081 mmol), and Potassium carbonate (0.806 ml, 1.612 mmol) in DMF. The solution was heated in the microwave for 15 minutes at 120° C. The reaction was cooled to room temperature. Diluted with water, extracted with ethyl acetate, combined organics, dried, filtered and concentrated. Purified by Combiflash column using 0% to 80% ethyl acetate in hexanes to afford tert-butyl (2-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)phenyl)carbamate (0.13 g, 0.361 mmol, 44.7% yield).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurified by Combiflash column

Sources & evidence

ORD record
ord-927c59a201ee489fb6a35edfae22ade2
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691187B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes