Toluene → HCID 24901900, compound

HRID 603461Notes

Reaction equation

HRID 603461 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[O:9]1[CH2:14][CH2:13][O:12][CH2:11]C1.C(Cl)Cl.[O-]S([O-])(=O)=O.[Na+].[Na+].[C:25]1(C)[CH:30]=CC=[CH:27][CH:26]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:9]1[C:14]2[CH:30]=[CH:25][C:26]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)=[CH:27][C:13]=2[O:12][CH2:11]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 312751,4-DioxaneHCID 775312,4-Dichloropyrimidine

Product 1

HCID 24901900HCID 24901900, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
75 °C

Procedure

To a mixture of 3,4-dioxolanephenylboronic acid (0.938 g, 5.54 mmol) and 2,4-dichloropyrimidine (1 g, 6.65 mmol) in toluene (112 mL) were added 1,4-dioxane (14 mL) and PdCl2(dppf).CH2Cl2 (0.452 g, 0.554 mmol). The mixture was purged with argon for 15 min after which a 2M aqueous solution of Na2SO4 (28 mL, 56 mmol) was added. The reaction mixture was stirred at 75° C. for 24 h, cooled to rt, and then washed with saturated solution of NaHCO3. The organic layer was separated from the mixture, and the aqueous phase extracted with EtOAc. The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then purified by silica gel flash chromatography (1:5 EtOAc/Hexanes) to give the product (324 mg, 25%) as crystalline white needles. 1H NMR (400 MHz, acetone-d6): δ 6.15 (s, 2H), 7.18 (d, 1H), 7.70 (d, 1H), 7.84 (d, 1H), 7.96 (d, 1H), 8.71 (d, 1H); LC-MS: RT=2.65 min, (M+H)+ 235.2.

Workup

  1. additionwas added
  2. temperaturecooled to rt
  3. washwashed with saturated solution of NaHCO3
  4. customThe organic layer was separated from the mixture
  5. extractionthe aqueous phase extracted with EtOAc
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was then purified by silica gel flash chromatography (1:5 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e578073cdccc46c597dc9286371e29ef
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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