Sodium Carbonate → HCID 57839036, compound

HRID 732959Notes

Reaction equation

HRID 732959 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[N:5]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=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>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:6]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:3]=[C:4]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 57839032HCID 57839032, compound

Product 1

HCID 57839036HCID 57839036, compoundYield 44.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 4-chloro-6-(2,4-dichlorophenyl)-2-phenylpyrimidine-5-carboxylate (30 mg, 0.07 mmol) and phenyl boronic acid (14 mg, 0.11 mmol) in toluene (3 mL) was degassed with argon for 15 minutes. To this solution was added Pd(PPh3)4 (9 mg, 0.007 mmol), Na2CO3 (23 mg, 0.22 mmol) and the reaction was heated to reflux for 3 days. The reaction was diluted with EtOAc (20 mL) and extracted with saturated NH4Cl solution (2×20 mL), brine (20 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The crude reaction product was purified by flash chromatography (silica gel, 20% EtOAc/hexane) to give ethyl 4-(2,4-dichlorophenyl)-2,6-diphenylpyrimidine-5-carboxylate (14 mg, 42%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 days
  3. extractionextracted with saturated NH4Cl solution (2×20 mL), brine (20 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude reaction product
  8. customwas purified by flash chromatography (silica gel, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-a1615aea21ee4e47a48f69e251bea0d4
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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