Water → HCID 86688750, compound

HRID 2275451Notes

Reaction equation

HRID 2275451 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)=[N:6][CH:7]=1.[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>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.C(#N)C>[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 86688751HCID 86688751, compound

Product 1

HCID 86688750HCID 86688750, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Then, 0.91 g of 5-bromo-2-(3,5-dimethylphenyl)pyrimidine, 1.05 g of 2,6-dimethylphenylboronic acid, 0.74 g of sodium carbonate, 0.029 g of bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2), 13 mL of water, and 13 mL of acetonitrile were put into a recovery flask equipped with a reflux pipe, and the mixture was bubbled with argon for 15 minutes. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 4 hours to be heated. Here, into the flask were further put 1.07 g of 2,6-dimethylphenylboronic acid, 0.73 g of sodium carbonate, and 0.029 g of Pd(PPh3)2Cl2, and the mixture was bubbled with argon for 15 minutes. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) again for 3 hours to be heated. After that, the obtained mixture was suction-filtered with water. The obtained solid was purified by flash column chromatography using toluene and hexane as a developing solvent in a ratio of 1:1, so that Hdmppm2-dmp (abbreviation), which was the pyrimidine derivative to be produced, was obtained as a white powder in a yield of 83%. A synthesis scheme of Step 2 is shown in (i-2).

Workup

  1. customequipped with a reflux pipe
  2. customthe mixture was bubbled with argon for 15 minutes
  3. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 4 hours
  4. temperatureto be heated
  5. customthe mixture was bubbled with argon for 15 minutes
  6. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) again for 3 hours
  7. temperatureto be heated
  8. filtrationAfter that, the obtained mixture was suction-filtered with water
  9. customThe obtained solid was purified by flash column chromatography
  10. customto be produced
  11. customwas obtained as a white powder in a yield of 83%
  12. customA synthesis scheme of Step 2

Sources & evidence

ORD record
ord-ca197074af644450b321bb4141ef4782
Source dataset
uspto-grants-2015_09
Patent number
US09127032B2

Reaction notes

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