Benzimidazole → HCID 22731922, 화합물

HRID 2083902노트

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HRID 2083902 반응식
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.[Br:12][C:13]1[C:14](Cl)=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1.C(OCC)(=O)C>CN(C=O)C.O>[Br:12][C:13]1[C:14]([N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1

참가 물질

7

반응물 4

HCID 5798BenzimidazoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2899735-Bromo-2,4-dichloropyrimidine

생성물 1

HCID 22731922HCID 22731922, 화합물수율 64.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

Sodium hydride (60% dispersion in oil; 110 mg, 2.75 mmol) was added to a solution of benzimidazole (295 mg, 2.5 mmol) in DMF (6 ml) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then added dropwise to a cold (0° C.) solution of 5-bromo-2,4-dichloropyrimidine (712 mg, 3.14 mmol) in DMF (6 ml). The mixture was stirred for at 0° C. for 2 hours and then ethyl acetate (20 ml) and water (20 ml) were added. The organic phase was separated and dried and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 20% ethyl acetate/DCM, to give the product as a white solid (500 mg, 52%). NMR: 7.4 (m, 2H), 7.8 (m, 2H), 8.8 (s, 1H), 9.3 (s, 1H); MS (MH+): 309, 311.

후처리

  1. stirringThe mixture was stirred for at 0° C. for 2 hours
  2. customThe organic phase was separated
  3. customdried
  4. customvolatile material was removed by evaporation
  5. customThe residue was purified by column chromatography
  6. washeluting with 20% ethyl acetate/DCM

출처 및 근거

ORD 기록
ord-bbb9f9b599e94bc3b7034752dc086bb6
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716831B1

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