Hydrochloric Acid → N-{3-Bromo-5-[(methylsulfanyl)methyl]phenyl}-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-amine

HRID 2277755노트

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HRID 2277755 반응식
Cl.O1CCOCC1.Cl[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[O:22][CH3:23])[C:12]([F:24])=[CH:11][N:10]=1.[Br:25][C:26]1[CH:27]=[C:28]([CH:30]=[C:31]([CH2:33][S:34][CH3:35])[CH:32]=1)[NH2:29]>C(O)CCC.C(OCC)(=O)C>[Br:25][C:26]1[CH:27]=[C:28]([NH:29][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[O:22][CH3:23])[C:12]([F:24])=[CH:11][N:10]=2)[CH:30]=[C:31]([CH2:33][S:34][CH3:35])[CH:32]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 867296092-Chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidineHCID 894447523-Bromo-5-[(methylsulfanyl)methyl]aniline

생성물 1

HCID 89444631N-{3-Bromo-5-[(methylsulfanyl)methyl]phenyl}-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-amine수율 46%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

A 4N solution of hydrogen chloride in dioxane (0.54 mL; 2.15 mmol) was added to a stirred solution of 2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (553 mg; 2.15 mmol) and 3-bromo-5-[(methylsulfanyl)methyl]aniline (500 mg; 2.15 mmol) in 1-butanol (4.8 mL). The batch was stirred at 140° C. for 8 hours. After cooling the batch was diluted with ethyl acetate and washed with sodium bicarbonate and saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatman filter and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 4:1) to give the desired product (450 mg; 0.99 mmol).

후처리

  1. temperatureAfter cooling the batch
  2. washwashed with sodium bicarbonate and saturated aqueous sodium chloride solution
  3. filtrationThe organic phase was filtered
  4. filtrationfilter
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (hexane/ethyl acetate 4:1)

출처 및 근거

ORD 기록
ord-3d69db03f8594a7e898c8ea8dfda43ef
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133171B2

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