Potassium Carbonate → HCID 59852879, compound

HRID 1670205Notes

Reaction equation

HRID 1670205 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N: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+]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([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:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 3014069Acetamide, N-(3-fluoro-4-hydroxyphenyl)-

Product 1

HCID 59852879HCID 59852879, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4,6-dichloropyrimidine (1.50 g, 10.0 mmol), N-(3-fluoro-4-hydroxyphenyl)acetamide (1.70 g, 10.0 mmol), K2CO3 (1.8 g, 13.0 mmol), and DMF (15 mL) was heated at 70° C. for 1.5 h. The mixture was concentrated to half its original volume and cooled in an ice bath. The mixture was treated with H2O (100 mL) to precipitate the product which was collected by vacuum filtration. The product was washed with H2O and vacuum dried on the funnel overnight to give the title compound (2.0 g, 71%) as a gray solid. 1H NMR (DMSO-d6) δ 10.26 (s, 1H), 8.67 (s, 1H), 7.78 (dd, 1H, J=12.6, 2.0 Hz), 7.56 (s, 1H), 7.37-7.30 (m, 2H), 2.08 (s, 3H); MS (ESI+) m/z 282.10 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated to half its original volume
  2. temperaturecooled in an ice bath
  3. additionThe mixture was treated with H2O (100 mL)
  4. customto precipitate the product which
  5. filtrationwas collected by vacuum filtration
  6. washThe product was washed with H2O and vacuum
  7. customdried on the funnel overnight

Sources & evidence

ORD record
ord-f2d6878687ba48e0a210a8959619c1b4
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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