Sodium Carbonate → HCID 136337209, compound

HRID 1891232Notes

Reaction equation

HRID 1891232 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[OH:9][C:10]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>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>[Cl:1][C:2]1[N:7]=[C:6]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([F:19])([F:18])[F:17])[C:10]=2[OH:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 46739026[2-Hydroxy-3-(trifluoromethyl)phenyl]boronic acid

Product 1

HCID 136337209HCID 136337209, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A vial was charged with 2,4-dichloropyrimidine (362 mg, 2.43 mmol), 2-hydroxy-3-trifluoromethylphenylboronic acid (250 mg, 1.21 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (42.6 mg, 0.061 mmol). Acetonitrile (6 mL) and sodium carbonate (3.0 mL, 1.0 M aqueous, 3.0 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 6 h, then was allowed to cool to ambient temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 25% EtOAc in hexanes, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 275.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 13.43 (s, 1H), 8.74 (d, J=5.5 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.76 (app d, J=5.5 Hz, 2H), 7.06 (t, J=8.0 Hz, 1H).

Workup

  1. customthe resulting mixture was degassed via nitrogen
  2. customsparge
  3. temperatureto cool to ambient temperature
  4. additionwas poured into water
  5. extractionThe mixture was extracted with EtOAc
  6. concentrationthe organic phase was concentrated in vacuo
  7. customPurification by chromatography on silica gel (0 to 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-c30d3410136e4650b248eada98ca36db
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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