Potassium Carbonate → N-(3-(5-bromo-2-chloropyrimidin-4-yl)phenyl)acrylamide

HRID 2368180Notes

Reaction equation

HRID 2368180 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]([NH:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)(=[O:13])[CH:11]=[CH2:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]([C:17]2[CH:16]=[C:15]([NH:14][C:10](=[O:13])[CH:11]=[CH2:12])[CH:20]=[CH:19][CH:18]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 103213313-Acrylamidophenylboronic acid

Product 1

HCID 71469245N-(3-(5-bromo-2-chloropyrimidin-4-yl)phenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

5-bromo-2,4-dichloropyrimidine (100 mg, 0.439 mmol), (3-acrylamidophenyl)boronic acid (50 mg, 0.262 mmol) and triphenylphosphine (4 mg, 0.018 mmol) were dissolved in a mixture of toluene (8 mL) and potassium carbonate (14 mg, 0.043 mmol), after which palladium(II) acetate (2 mg, 0.009 mmol) was added. The reaction mixture was allowed to stir overnight at 40° C. The reaction was monitored by TLC, and after completion of the reaction the solvent was removed in vacuo. The crude material was purified by flash chromatography (EtOAc/Hexane 20%) to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.51 (s, 1H), 7.64 (s, 1H), 7.38-7.29 (m, 2H), 6.85 (m, 1H), 6.38-6.21 (m, 2H), 5.69 (dd, 1H, J=1.6 & 10.0 Hz). ESI-MS: m/z 339.90 [M+H]+.

Workup

  1. customafter completion of the reaction the solvent
  2. customwas removed in vacuo
  3. customThe crude material was purified by flash chromatography (EtOAc/Hexane 20%)

Sources & evidence

ORD record
ord-e35e3253a66940a299cec11d1fc4811e
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

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