3-[6-(2-Fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-(3-diethylaminopropyl)-1-methylurea → 3-[6-(4-Amino-2-fluorophenoxy)pyrimidin-4-yl]-1-(3-diethylaminopropyl)-1-methylurea

HRID 492763노트

반응식

HRID 492763 반응식
[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:23])[N:13]([CH2:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:14])[CH:6]=1.[H][H]>O1CCCC1.CO.[C].[Pd]>[NH2:28][C:26]1[CH:25]=[CH:24][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:23])[N:13]([CH2:15][CH2:16][CH2:17][N:18]([CH2:19][CH3:20])[CH2:21][CH3:22])[CH3:14])[CH:6]=2)=[C:2]([F:1])[CH:27]=1

참가 물질

6

반응물 2

HCID 231532583-[6-(2-Fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-(3-diethylaminopropyl)-1-methylureaHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 231534393-[6-(4-Amino-2-fluorophenoxy)pyrimidin-4-yl]-1-(3-diethylaminopropyl)-1-methylurea수율 68.6%

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

3-[6-(2-Fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-(3-diethylaminopropyl)-1-methylurea (54.0 mg) was dissolved in tetrahydrofuran (2 ml)-methanol (2 ml), and then 10% palladium carbon (27.2 mg) was added thereto, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with methanol. The filtrate was concentrated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1, then ethyl acetate). Fractions containing the target compound were concentrated under a reduced pressure to provide the titled compound (34.3 mg, 68.6%) as a pale yellow solid.

후처리

  1. filtrationthe reaction mixture was filtered
  2. customto remove the catalyst, which
  3. washwas washed with methanol
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customto give a residue, which
  6. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent
  7. additionFractions containing the target compound
  8. concentrationwere concentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-4894bd119944433eb78cfc6826d20250
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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