Water → N-(4-(6-(3-Fluorophenylamino)pyrimidin-4-yloxy)phenyl)-N'-phenylurea

HRID 388001Notes

Reaction equation

HRID 388001 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:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29].O>CN1CCCC1=O.C(OCC)(=O)C.CCCCCC>[F:25][C:26]1[CH:27]=[C:28]([NH:29][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:30]=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 962WaterHCID 97423-FluoroanilineHCID 22937019N-(4-(6-Chloropyrimidin-4-yloxy)phenyl)-N'-phenylurea

Product 1

HCID 22936950N-(4-(6-(3-Fluorophenylamino)pyrimidin-4-yloxy)phenyl)-N'-phenylureaYield 52%

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 3-fluoroaniline (111 mg, 1.00 mmol) were heated and stirred in 1-methylpyrrolidone (1 ml) at 150° C. for 90 minutes. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with saturated aqueous sodium bicarbonate, water and saturated saline 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 (43.0 mg, 0.104 mmol, 52%) as colorless crystals.

Workup

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate, water and saturated saline
  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-eb04e83494124ca7b6a2cd663e0f9a45
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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