Sodium Carbonate → HCID 54161279, compound

HRID 1626450Notes

Reaction equation

HRID 1626450 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 5889352-Chloro-4-methoxypyrimidine

Product 1

HCID 54161279HCID 54161279, compoundYield 20.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

2-Chloro-4-methoxypyrimidine (509 mg, 3.52 mmol), 4-chlorophenylboronic acid (826 mg, 5.28 mmol), and sodium carbonate (3732 μl, 7.04 mmol) in toluene (17 ml) were sparged with argon for 2 minutes in a glass vial. Pd(PPh3)4 (203 mg, 0.176 mmol) was added and the reaction mixture was sparged an additional 1 minute. The vial was capped and the reaction heated to 115° C. for 19 hours. The reaction was cooled to ambient temperature and diluted with ethyl acetate. The organic layer was washed with water and brine, dried with sodium sulfate, filtered, concentrated and purified on silica gel. Elution with a 2-20% ethyl acetate/hexanes gradient provided the title compound (161 mg, 0.730 mmol, 20.7% yield) as a white foam.

Workup

  1. customthe reaction mixture was sparged an additional 1 minute
  2. customThe vial was capped
  3. temperatureThe reaction was cooled to ambient temperature
  4. additiondiluted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on silica gel
  10. washElution with a 2-20% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-5db240040da54277b938fc783dab1d62
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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