Potassium Carbonate → HCID 59852879, compound

HRID 2237174Notes

Reaction equation

HRID 2237174 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-331e829ef03744ef8fa4767ef6831114
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Reaction notes

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