Water → N-Phenyl-N'-(4-(6-phenylaminopyrimidin-4-yloxy)phenyl)urea

HRID 853516Notes

Reaction equation

HRID 853516 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)=[CH:4][CH:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[C:22]1([NH:28][C:29]([NH:1][C:2]2[CH:21]=[CH:20][C:5]([O:6][C:7]3[CH:8]=[C:9]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:10]=[CH:11][N:12]=3)=[CH:4][CH:3]=2)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 22936405N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine

Product 1

HCID 22936423N-Phenyl-N'-(4-(6-phenylaminopyrimidin-4-yloxy)phenyl)ureaYield 87%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine (55.6 mg, 0.200 mmol) and phenyl isocyanate (26.1 mg, 0.220 mmol) were stirred together in dimethylformamide (1 ml) at room temperature for 12 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (69.0 mg, 0.174 mmol, 87%) as colorless crystals.

Workup

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried

Sources & evidence

ORD record
ord-1629e0316ebe4e05acac0807a3cb9c0d
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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