2-Amino-5-bromopyrimidine → HCID 90411524, compound

HRID 930825Notes

Reaction equation

HRID 930825 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[Cl:14])=O.[Br:15][C:16]1[CH:17]=[N:18][C:19]([NH2:22])=[N:20][CH:21]=1>C(O)C>[Br:15][C:16]1[CH:17]=[N:18][C:19]2[N:20]([CH:2]=[C:3]([C:5]3[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=3[Cl:14])[N:22]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 2313102-Amino-5-bromopyrimidineHCID 12273165HCID 12273165, compound

Product 1

HCID 90411524HCID 90411524, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(2-chloro-5-nitrophenyl)ethan-1-one (I-2) (30 g, 108 mmol, 1.00 equiv) and 5-bromopyrimidin-2-amine (15 g, 88 mmol, 0.81 equiv) in ethanol (300 ml) was stirred for 12 h at 75° C. and then concentrated under vacuum. The residue was diluted with 200 ml of water and extracted with 3×100 ml of ethyl acetate. The combined organic layers was washed with brine, dried over Na2SO4 and concentrated under vacuum to give 15 g (39%) of 6-bromo-2-(2-chloro-5-nitrophenyl)imidazo[1,2-a]pyrimidine (I-3) as a brown solid.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was diluted with 200 ml of water
  3. extractionextracted with 3×100 ml of ethyl acetate
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-13c2fc4ecf0944db8660de27698fbd5f
Source dataset
uspto-grants-2016_03
Patent number
US09296754B2

Reaction notes

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