Sodium Carbonate → HCID 71469141, compound

HRID 1500792Notes

Reaction equation

HRID 1500792 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[C:16]([NH:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)(=[O:19])[CH:17]=[CH2:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:23]2[CH:22]=[C:21]([NH:20][C:16](=[O:19])[CH:17]=[CH2:18])[CH:26]=[CH:25][CH:24]=2)[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 103213313-Acrylamidophenylboronic acidHCID 57498061HCID 57498061, compound

Product 1

HCID 71469141HCID 71469141, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

2,4-Dichloro-N-phenylpyrimidin-5-amine (80 mg, 0.333 mmol), (3-acrylamidophenyl)-boronic acid (70.0 mg, 0.367 mmol), triphenylphosphine (3.50 mg, 0.013 mmol) and palladium acetate (1.496 mg, 6.66 μmol) were dissolved in toluene (8 mL) and 1M sodium carbonate (70.6 mg, 0.666 mmol). The reaction mixture was heated for 24 h at 90° C., allowed to cool to room temperature, and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (20 mL) and washed with water (10 mL). The organic layer was separated, the aqueous layer was extracted with ethyl acetate (20 mL), the combined organic layers were washed with brine (20 mL), and dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography (20% ethyl acetate/hexane) to the title compound. 1H NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 7.89 (s, 1H), 7.74 (s, 1H), 7.66 (d, 1H, J=8.4 Hz), 7.49 (d, 1H, J=8.0 Hz), 7.38 (t, 1H, J=8.0 Hz), 7.30 (m, 2H), 7.09-7.03 (m, 3H), 6.39 (m, 1H), 6.20 (m, 1H), 6.09 (dd, 1H, J=10.4 and 17.2 Hz), 5.75 (d, 1H, J=10.4 Hz); ESI-MS: 351.1 [M+H]+.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  4. washwashed with water (10 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (20 mL)
  7. washthe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography (20% ethyl acetate/hexane) to the title compound

Sources & evidence

ORD record
ord-fd728284ae16451d9d46411915724a2f
Source dataset
uspto-grants-2015_12
Patent number
US09206176B2

Reaction notes

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