Pyridine → N-(6-(4-(3-Phenylureido)phenoxy)pyrimidin-4-yl)acetamide

HRID 387984Notes

Reaction equation

HRID 387984 reaction equation
[NH2:1][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.[C:25](OC(=O)C)(=[O:27])[CH3:26].N1C=CC=CC=1>O>[C:19]1([NH:18][C:16](=[O:17])[NH:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:1][C:25](=[O:27])[CH3:26])[CH:3]=3)=[CH:14][CH:13]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22936842N-(4-(6-Aminopyrimidin-4-yloxy)phenyl)-N'-phenylurea

Product 1

HCID 22936729N-(6-(4-(3-Phenylureido)phenoxy)pyrimidin-4-yl)acetamideYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(4-(6-Aminopyrimidin-4-yloxy)phenyl)-N′-phenylurea (60.0 mg, 0.187 mmol) was heated and stirred in an acetic anhydride (1 ml)-pyridine (1 ml) mixed solvent at 60° C. for 18 hours. After returning the reaction solution to room temperature, it was poured into water and the precipitated crystals were filtered out, washed with water and methanol and blow-dried to obtain the title compound (35.0 mg, 0.096 mmol, 52%) as colorless crystals.

Workup

  1. additionmixed solvent at 60° C. for 18 hours
  2. customto room temperature
  3. filtrationthe precipitated crystals were filtered out
  4. washwashed with water and methanol
  5. customblow-dried

Sources & evidence

ORD record
ord-9eb03d708cb143978bf05a72f4a558f5
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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