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 492763Notes

Reaction equation

HRID 492763 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4894bd119944433eb78cfc6826d20250
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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