4-[(2-Methoxyethoxy)methoxy]aniline → 5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamine

HRID 2274247노트

반응식

HRID 2274247 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:5]([F:18])=[CH:4][N:3]=1.[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.CCCCCC.C(OCC)(=O)C>C(O)C.C(O)(=O)C>[F:18][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[N:7][C:2]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([O:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH3:19])=[CH:27][CH:28]=2)=[N:3][CH:4]=1

참가 물질

6

반응물 3

HCID 131356894-[(2-Methoxyethoxy)methoxy]anilineHCID 21226206Ethyl acetate hexaneHCID 591746392-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine

생성물 1

HCID 867243285-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamine수율 62.6%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 702Ethanol용매2회

실험 절차

To a solution of 2-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine (0.400 g) and 4-[(2-methoxyethoxy)methoxy]aniline (0.458 g), in ethanol (20 mL), was added acetic acid (4.65 mg). The reaction mixture was heated to reflux for 24 hr. Completion of reaction was monitored by TLC using hexane:ethyl acetate (8:2) as mobile phase. After completion of the reaction, ethanol was removed under reduced pressure at 40° C. To the residue water (25 mL) was added and mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and distilled under reduced pressure to give 0.4 g of 5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamine as a solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hr
  3. customCompletion of reaction
  4. customwas removed under reduced pressure at 40° C
  5. additionTo the residue water (25 mL) was added
  6. extractionmixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. distillationdistilled under reduced pressure

출처 및 근거

ORD 기록
ord-ad504a34985d43beac04d8cd4c8d0dfa
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126950B2

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