Sodium Carbonate → HCID 46897435, compound

HRID 220065Notes

Reaction equation

HRID 220065 reaction equation
O1CCOCC1.Cl[C:8]1[C:13]([NH:14][C:15](=[O:24])[C:16]2[CH:21]=[CH:20][CH:19]=[N:18][C:17]=2[CH2:22][CH3:23])=[C:12]([NH:25][CH:26]2[CH2:28][CH2:27]2)[N:11]=[CH:10][N:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:35][C:36]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=1B(O)O>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>[CH:26]1([NH:25][C:12]2[C:13]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][CH:19]=[N:18][C:17]=3[CH2:22][CH3:23])=[C:8]([C:39]3[CH:38]=[CH:37][C:36]([Cl:35])=[CH:41][C:40]=3[Cl:42])[N:9]=[CH:10][N:11]=2)[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 46897521HCID 46897521, compound

Product 1

HCID 46897435HCID 46897435, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

In a test tube which had been dried by heating and preheated to 100° C., the degassed diluent mixture dioxane (2 ml)/water (0.7 ml) was added to N-(4-chloro-6-cyclopropylaminopyrimidin-5-yl)-2-ethylnicotinamide (0.41 mmol), sodium carbonate (3 eq) and 2,4-dichlorophenylboronic acid (2 eq). 5 mol % of tetrakis(triphenylphosphine)palladium(0) were added, and the reaction mixture was stirred at 90° C. for 3 hours. The mixture was then diluted with water and extracted 3× with methylene chloride, and the combined organic phases were washed with aqueous NaHCO3 solution, dried 20 over Na2SO4, filtered and concentrated under reduced pressure.

Workup

  1. customIn a test tube which had been dried
  2. temperatureby heating
  3. custompreheated to 100° C.
  4. extractionextracted 3× with methylene chloride
  5. washthe combined organic phases were washed with aqueous NaHCO3 solution
  6. dry with materialdried 20 over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21ed0125a87d403288fbcbfa4761051e
Source dataset
uspto-grants-2012_06
Patent number
US08202877B2

Reaction notes

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