Water → N-(4-(6-(4-Fluorophenylamino)pyrimidin-4-yloxy)phenyl)-N'-phenylurea

HRID 1010385Notes

Reaction equation

HRID 1010385 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:3]=1.[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.O>CN1CCCC1=O.C(OCC)(=O)C.CCCCCC>[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:2]2[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:17])=[CH:11][CH:10]=3)[CH:3]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 962WaterHCID 97314-FluoroanilineHCID 22937019N-(4-(6-Chloropyrimidin-4-yloxy)phenyl)-N'-phenylurea

Product 1

HCID 22936820N-(4-(6-(4-Fluorophenylamino)pyrimidin-4-yloxy)phenyl)-N'-phenylureaYield 40%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-(4-(6-Chloropyrimidin-4-yloxy)phenyl)-N′-phenylurea (68.0 mg, 0.200 mmol) and 4-fluoroaniline (111 mg, 1.00 mmol) were heated and stirred in 1-methylpyrrolidone (1 ml) at 130° C. for 3 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with saturated aqueous sodium bicarbonate, 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 (33.0 mg, 0.079 mmol, 40%) as colorless crystals.

Workup

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate, 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-2b4c0b5a1c164d40a8a45eaa73f28bda
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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