Potassium Carbonate → HCID 59852879, compound

HRID 2373953Notes

Reaction equation

HRID 2373953 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-c7fb4a60548e4ecb91ea3e4f917605dd
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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