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

HRID 401463

반응식

HRID 401463 반응식
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

참가 물질

4

반응물 2

HCID 749452-BromopropanedialHCID 2313102-Amino-5-bromopyrimidine

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c18854e5a8b942e58362760cfd91c728
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741932B2

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