Sodium Carbonate → HCID 59772764, compound

HRID 646219Notes

Reaction equation

HRID 646219 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18](Br)[CH:17]=2)([C:9]2[CH:13]=[CH:12][N:11]([CH2:14][CH3:15])[CH:10]=2)[N:3]=1.[N:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[N:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:9]2[CH:13]=[CH:12][N:11]([CH2:14][CH3:15])[CH:10]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:27]3[CH:28]=[N:23][CH:24]=[N:25][CH:26]=3)[CH:17]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59772709HCID 59772709, compound

Product 1

HCID 59772764HCID 59772764, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-amino-5-(3-bromophenyl)-5-(1-ethyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (80 mg, 0.22 mmol) in DME (3 mL) is added pyrimidin-5-ylboronic acid (57 mg, 0.44 mmol), tetrakis(triphenylphosphine)palladium (25 mg, 0.022 mmo) and a solution sodium carbonate (93 mg, 0.88 mmol) in H2O (0.5 mL) at room temperature. The reaction mixture is refluxed for 1 h and cooled. After evaporation of the solvent, the crude material is purified by chromatography (silica gel, EtOAc/2M ethanolic NH3: 92/8) to give the title compound (60 mg, 75%) as a solid. mp: 100-102° C.; MS (+) ES: 361 (M+H)+.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture is refluxed for 1 h
  3. temperaturecooled
  4. customAfter evaporation of the solvent
  5. customthe crude material is purified by chromatography (silica gel, EtOAc/2M ethanolic NH3: 92/8)

Sources & evidence

ORD record
ord-4b1303940aaf4f74ab3f80e0133d8699
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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