Sodium Carbonate → HCID 70979645, compound

HRID 1403218Notes

Reaction equation

HRID 1403218 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11](Br)=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+].[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([CH3:37])=[C:32](B(O)O)[CH:33]=1>CCO.C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:30]3[CH:29]=[C:28]([Cl:27])[CH:33]=[CH:32][C:31]=3[CH3:37])=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 49788132HCID 49788132, compound

Product 1

HCID 70979645HCID 70979645, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 5-(2-aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxylate (prepared according to WO2007/110344, 2.0 g, 6.43 mmol) dissolved in EtOH (20 mL) and toluene (20 mL), LiCl (408 mg, 9.64 mmol), 1 M aq Na2CO3 (17 mmol), 5-chloro-2-methylphenylboronic acid (1.423 g, 8.35 mmol) and Pd(Ph3P)2Cl2 (470 mg, 0.67 mmol) were added and the reaction mixture was heated at 100° C. for 5 h. After cooling to room temperature, the precipitate was filtered and the filtrate was evaporated under reduced pressure, dissolved in DCM and washed with water. The organic layer was then dried over sodium sulfate and concentrated. The crude material was chromatographed on silica gel (DCM/EtOAc 50/50) to afford the title compound (1.99 g, 87%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutiondissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic layer was then dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude material was chromatographed on silica gel (DCM/EtOAc 50/50)

Sources & evidence

ORD record
ord-c1581db90e294fcb9ed002a2958b65dc
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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