Potassium Carbonate → HCID 59852996, compound

HRID 1670240Notes

Reaction equation

HRID 1670240 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:11]=[C:12]([NH:17][C:18](=[O:20])[CH3:19])[CH:13]=[CH:14][C:15]=1[OH:16].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:1][C:2]1[N:7]=[C:6]([O:16][C:15]2[CH:14]=[CH:13][C:12]([NH:17][C:18](=[O:20])[CH3:19])=[CH:11][C:10]=2[F:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 3014069Acetamide, N-(3-fluoro-4-hydroxyphenyl)-

Product 1

HCID 59852996HCID 59852996, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-dichloropyrimidine (Aldrich, 1.5 g, 10.0 mmol), N-(3-fluoro-4-hydroxyphenyl)acetamide (0.85 g, 5.0 mmol), K2CO3 (0.76 g, 5.5 mmol), and CH3CN (100 mL) was heated at reflux for 2 h. The mixture was concentrated and the residue partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc phase was washed with sat NaHCO3 solution, brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient form 30% EtOAc in hexanes to 100% EtOAc to give the title compound (1.1 g, 78%) as a white solid. 1H NMR (DMSO-d6) δ 10.22 (s, 1H), 8.63 (d, 1H, J=5.6 Hz), 7.74 (dd, 1H, J=12.6, 2.4 Hz), 7.34-7.26 (m, 3H), 2.01 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. customthe residue partitioned between EtOAc and saturated NaHCO3 solution
  5. washThe EtOAc phase was washed with sat NaHCO3 solution, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-91b1cf995cba448c8e33314f28351592
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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