Urea → HCID 57662913, compound

HRID 406828Notes

Reaction equation

HRID 406828 reaction equation
NC1C=CC=CC=1C1C([C:14]([C:16]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH2:28])=[CH:20][CH:19]=[CH:18][N:17]=2)=O)=NC=CC=1.[NH2:29][C:30](N)=[O:31]>C(O)(=O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:14][C:16]=1[C:21]1[C:22]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:28][C:30](=[O:31])[N:29]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 68924224HCID 68924224, compound

Product 1

HCID 57662913HCID 57662913, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-aminophenyl-2-pyridyl ketone (0.95 g, 4.8 mmol), urea (500 mg, 8.3 mmol) and acetic acid (10 mL) was stirred at 110° C. for 18 h. The reaction mixture was cooled to rt and filtered. The solid was washed with water and dried under reduced pressure to give 4-(pyridin-2-yl)quinazolin-2(1H)-one as a yellow solid (0.83 g, 78%), which was dissolved in phosphorous oxychloride (3 mL) and the mixture was stirred at reflux for 30 min. The reaction mixture was cooled to rt and slowly poured over an ice/water mixture. The mixture was filtered and the solid was dried under reduced pressure to give 2-chloro-4-(pyridin-2-yl)quinazoline as an off-white solid (56 mg, 6%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-fefabd449665410f921229ec5fe999b5
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

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