Sodium Carbonate → HCID 57445459, compound

HRID 2189178Notes

Reaction equation

HRID 2189178 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH2:10]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O)[CH2:11][CH:12]([CH3:14])[CH3:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:15][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[N:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 773782,4,6-TrichloropyrimidineHCID 43145275HCID 43145275, compound

Product 1

HCID 57445459HCID 57445459, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,4,6-trichloropyrimidine (7.32 g, 40 mmol) in 40 mL of THF was added 2-(isopentyloxy)phenylboronic acid (4.1 g, 20 mmol), Pd(OAc)2 (0.4 mmol), PPh3 (0.8 mmol), and Na2CO3 solution (40 mL, 1M). The reaction was heated to 60° C. for 3 hours with stirring. The resulting mixture was cooled down to room temperature then partitioned between EtOAc and water. Layers were separated, and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography to result in 4.3 g (70%) of 2,4-dichloro-6-(2-(isopentyloxy)phenyl)pyrimidine as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.18-8.14 (m, 2H), 7.45 (dd, 1H), 7.09 (t, 1H), 7.01 (t, 1H), 4.10 (t, 2H), 1.90-1.75 (m, 3H), 1.02 (s, 6H).

Workup

  1. temperatureThe resulting mixture was cooled down to room temperature
  2. customthen partitioned between EtOAc and water
  3. customLayers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography
  9. customto result in 4.3 g (70%) of 2,4-dichloro-6-(2-(isopentyloxy)phenyl)pyrimidine as a white solid

Sources & evidence

ORD record
ord-4d18157dc8fb491da805b313f35ca76c
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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