Dimethylformamide → HCID 59853028, compound

HRID 2359691Notes

Reaction equation

HRID 2359691 reaction equation
Cl[C:2]1([Cl:8])[NH:7][CH:6]=[N:5][CH:4]=[CH:3]1.CN(C)C=O.[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[OH:24].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[Cl:8][C:2]1[CH:3]=[C:4]([O:24][C:16]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=2[F:14])[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 98252-Fluoro-4-nitrophenolHCID 10796Cesium carbonateHCID 178478260HCID 178478260, compound

Product 1

HCID 59853028HCID 59853028, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6,6-dichloropyrimidine (1.000 g, 7 mmol) was dissolved in N,N-dimethylformamide (5 ml, 7 mmol), then 2-fluoro-4-nitrophenol (1 g, 7 mmol) was added into the mixture. Then Cesium Carbonate (2 g, 10 mmol) was added into the mixture with stirring. The mixture was stirred at ambient temperature under nitrogen overnight. The progress of the reaction was monitored by LC/MS, which had confirmed completion. Then diluted the mixture with water was stirred an additional 3 hours. The precipitate was collected by filtration and washed with hexanes. The solid was dried in a reduced-pressure oven overnight to give the desired product 4-chloro-6-(2-fluoro-4-nitrophenoxy)pyrimidine (1.500 g, 6 mmol, 83% yield) as a yellow solid. MS (ESI pos. ion) m/z: 270 (MH+). Calc'd exact mass for C10H5ClFN3O3: 269. 1HNMR (300 MHz, CDCl3): 7.14 (s, 1H), 7.43 (s, 1H), 8.14 (s, 2H), 8.55 (s, 1H).

Workup

  1. stirringThe mixture was stirred at ambient temperature under nitrogen overnight
  2. stirringwas stirred an additional 3 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with hexanes
  5. customThe solid was dried in a reduced-pressure oven overnight

Sources & evidence

ORD record
ord-85f7db140a934a15b0e1a0c91fb883f4
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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