Dimethylformamide → HCID 117774930, compound

HRID 1482166Notes

Reaction equation

HRID 1482166 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=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.O>[C:8]1([C:6]2[CH:7]=[C:2]([C:16]3[C:15]([CH3:14])=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:21])[N:3]=[CH:4][N:5]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 5934294-Chloro-6-phenylpyrimidine

Product 1

HCID 117774930HCID 117774930, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

Next, 1.6 g of 4-chloro-6-phenylpyrimidine synthesized in Step 1, 1.5 g of 2,6-dimethylphenylboronic acid, 1.8 g of sodium carbonate, 59 mg of PdCl2(PPh3)2, 20 mL of N,N-dimethylformamide (abbreviation: DMF), and 20 mL of water were put into a 100-mL round-bottom flask, and the air in the flask was replaced with argon. Then, heating was performed by irradiation with microwaves (2.45 GHz, 100 W) for 2 hours. An organic layer was extracted from the obtained mixture with the use of dichloromethane, and was washed with water and saturated brine. Magnesium sulfate was added and gravity filtration was performed. A solvent in the obtained filtrate was distilled off, and the given residue was purified by flash column chromatography using a mixed solvent of ethyl acetate and hexane (ethyl acetate: hexane=1:5) as a developing solvent, whereby 0.50 g of the objective substance, Hppm-dmp (abbreviation) was obtained (yield: 23%, a pale yellow oily substance). A synthesis scheme of Step 2 is shown in (a-2) below.

Workup

  1. temperatureThen, heating
  2. customwas performed by irradiation with microwaves (2.45 GHz, 100 W) for 2 hours
  3. extractionAn organic layer was extracted from the obtained mixture with the use of dichloromethane
  4. washwas washed with water and saturated brine
  5. additionMagnesium sulfate was added
  6. filtrationgravity filtration
  7. distillationA solvent in the obtained filtrate was distilled off
  8. customthe given residue was purified by flash column chromatography
  9. customHppm-dmp (abbreviation) was obtained (yield: 23%
  10. customA synthesis scheme of Step 2

Sources & evidence

ORD record
ord-55effa49d0d64b4aa46f5e9d17e7d189
Source dataset
uspto-grants-2016_08
Patent number
US09412956B2

Reaction notes

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