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

HRID 1010367Notes

Reaction equation

HRID 1010367 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=2)=[CH:4][CH:3]=1.[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[NH2:13][C:9]1[N:10]=[CH:11][N:12]=[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([NH:1][C:23]([NH:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:24])=[CH:3][CH:4]=2)[CH:8]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 229363746-(4-Amino-phenoxy)-pyrimidin-4-ylamine

Product 1

HCID 22936842N-(4-(6-Aminopyrimidin-4-yloxy)phenyl)-N'-phenylureaYield 69.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

6-(4-Aminophenoxy)pyrimidin-4-ylamine (88.9 mg, 0.440 mmol) and phenyl isocyanate (52.4 mg, 0.440 mmol) were stirred together for 3 hours in dimethylformamide (2 ml) at room temperature. 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 (98.0 mg, 0.305 mmol, 69%) 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-1b658877e9f54b348932d8eb9d458d59
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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