2-Amino-5-bromopyrimidine → 5-[4-(6-Bromoimidazo[1,2-a]pyrimidin-2-yl)phenyl]-1,3-oxazole

HRID 910222Notes

Reaction equation

HRID 910222 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][CH:22]=[N:21][CH:20]=2)=[CH:15][CH:14]=1)=O>O1CCOCC1>[Br:8][C:5]1[CH:4]=[N:3][C:2]2[N:7]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[O:23][CH:22]=[N:21][CH:20]=4)=[CH:15][CH:14]=3)[N:1]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 2313102-Amino-5-bromopyrimidineHCID 866318862-Bromo-1-[4-(1,3-oxazol-5-yl)phenyl]-1-ethanone

Product 1

HCID 674055005-[4-(6-Bromoimidazo[1,2-a]pyrimidin-2-yl)phenyl]-1,3-oxazoleYield 86.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Amino-5-bromopyrimidine (348 mg) and 2-bromo-1-[4-(1,3-oxazol-5-yl)phenyl]-1-ethanone (532 mg) were suspended in 1,4-dioxane (20 mL), followed by refluxing under heating overnight. Immediately after refluxing, the reaction mixture was filtered without being cooled, followed by washing with heated 1,4-dioxane and drying, to thereby yield the title compound (587 mg).

Workup

  1. temperatureby refluxing
  2. temperatureunder heating overnight
  3. temperatureImmediately after refluxing
  4. filtrationthe reaction mixture was filtered
  5. temperaturewithout being cooled
  6. washby washing with heated 1,4-dioxane
  7. customdrying

Sources & evidence

ORD record
ord-7d9150ae60a447fe97a2c80da206e44c
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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