2-Bromopropanedial → 6-Bromoimidazo[1,2-a]pyrimidine-3-carbaldehyde

HRID 401463

Reaction equation

HRID 401463 reaction equation
Br[CH:2]([CH:5]=[O:6])[CH:3]=O.[Br:7][C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1>C(#N)C>[Br:7][C:8]1[CH:9]=[N:10][C:11]2[N:12]([C:2]([CH:5]=[O:6])=[CH:3][N:14]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 749452-BromopropanedialHCID 2313102-Amino-5-bromopyrimidine

Product 1

HCID 717483586-Bromoimidazo[1,2-a]pyrimidine-3-carbaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromomalonaldehyde (500 mg, 2.90 mmol) was added to a solution of 5-bromopyrimidin-2-amine (526 mg, 3.49 mmol) in acetonitrile. The reaction mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was quenched with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The organic layer was concentrated and the product was purified by column chromatography using up to 2% methanol in chloroform gradient to obtain the title compound. Yield: 40%; 1H NMR (DMSO-d6; 300 MHz): δ 9.98(s, 1H), 9.75-9.76 (d, 1H, J=2.4 Hz), 8.97-8.98 (d, 1H, 2.4 Hz), 8.70 (s, 1H); MS (m/z): 226 (M+1)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched with sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe organic layer was concentrated
  8. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-c18854e5a8b942e58362760cfd91c728
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Linked notes

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