Phenacyl bromide → 2-Phenylimidazo[1,2-A]pyrimidin-7-amine

HRID 1958311Notes

Reaction equation

HRID 1958311 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12]1[N:17]=[C:16]([NH2:18])[CH:15]=[CH:14][N:13]=1>CC(C)=O>[C:5]1([C:3]2[N:11]=[C:12]3[N:17]=[C:16]([NH2:18])[CH:15]=[CH:14][N:13]3[CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 674312,4-Diaminopyrimidine

Product 1

HCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Bromoacetophenone (2.71 g, 14 mmol) was added to a solution of 2,4-diaminopyrimidine (1.00 g, 9 mmol) in acetone (40 ml), and the mixture was heated to reflux for 5 h. The cooled suspension was filtered, the precipitate was washed (acetone), and then stirred for 15 min in a mixture of 10 ml water and 15 ml NH4OH (25%). The suspension was filtered, washed (water), and dried under vacuum. The crude product (1.9 g, quant.) was used in the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 h
  3. filtrationThe cooled suspension was filtered
  4. washthe precipitate was washed (acetone)
  5. filtrationThe suspension was filtered
  6. washwashed (water)
  7. customdried under vacuum
  8. customThe crude product (1.9 g, quant.) was used in the next step without further purification

Sources & evidence

ORD record
ord-52ee05b790234f82837375508997b86c
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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