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

HRID 2277749노트

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HRID 2277749 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.[CH3:25][S:26][CH2:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31]>C(O)CCC.C(OCC)(=O)C>[F:24][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[O:22][CH3:23])=[N:14][C:9]([NH:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:28]([CH2:27][S:26][CH3:25])[CH:29]=2)=[N:10][CH:11]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 397333593-[(Methylsulfanyl)methyl]anilineHCID 867296092-Chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine

생성물 1

HCID 894443955-Fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine수율 72.2%

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 (0.61 mL; 2.45 mmol) was added to a stirred solution of 2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (630 mg; 2.45 mmol) and 3-[(methyl-sulfanyl)methyl]aniline (564 mg; 3.68 mmol) in 1-butanol (5.4 mL). The batch was stirred at 140° C. for 16 hours. After cooling the batch was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution 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 2:1) to give the desired product (662 mg; 1.77 mmol).

후처리

  1. temperatureAfter cooling the batch
  2. washwashed with aqueous sodium bicarbonate solution 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 2:1)

출처 및 근거

ORD 기록
ord-57844259a38f41d4ad8be1906f9a8075
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133171B2

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