Sodium Carbonate → HCID 627959, compound

HRID 713574Notes

Reaction equation

HRID 713574 reaction equation
Br[C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][C:7]=1Cl.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(#N)C.O>[C:10]1([C:3]2[C:2]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:6]=[CH:5][N:4]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 3

HCID 10340Sodium Carbonate2×HCID 66827Phenylboronic Acid2×HCID 111605Pyrimidine, 5-bromo-4,6-dichloro-

Product 1

HCID 627959HCID 627959, compoundYield 46%

Reagents, catalysts & solvents 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

First, into a recovery flask equipped with a reflux pipe were put 4.25 g of 5-bromo-4,6-dichloropyrimidine, 6.84 g of phenylboronic acid, 5.95 g of sodium carbonate, 0.16 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was heated by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes. Here, into the flask were further put 2.28 g of phenylboronic acid, 1.98 g of sodium carbonate, 0.053 g of Pd(PPh3)2Cl2, 5 mL of water, and 5 mL of acetonitrile, and the mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes. After that, the precipitated solid was suction-filtered and washed with water. The obtained residue was purified by flash column chromatography using dichloromethane and ethyl acetate as a developing solvent in a ratio of 10:1, so that a pyrimidine derivative Htppm, which was the objective substance, was obtained (white powder, yield of 46%). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme (1-1) of Step 1 is shown below.

Workup

  1. customFirst, into a recovery flask equipped with a reflux pipe
  2. temperatureThis reaction container was heated by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes
  3. temperaturethe mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes
  4. filtrationAfter that, the precipitated solid was suction-filtered
  5. washwashed with water
  6. customThe obtained residue was purified by flash column chromatography
  7. customwas obtained (white powder, yield of 46%)
  8. customNote that the irradiation with microwaves
  9. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  10. customA synthesis scheme (1-1) of Step 1

Sources & evidence

ORD record
ord-5f7b9d5a89914b308347d8c57ced599e
Source dataset
uspto-grants-2015_11
Patent number
US09184398B2

Reaction notes

Loading…