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3-Fluoro-4-(4-methylpiperazin-1-yl)aniline → 3-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-2-((3-fluorophenoxy)methyl)-6-methylpyrimidin-4(3H)-one

HRID 56258
Notes
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Reaction equation

HRID 56258 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)[NH2:5].C[Al](C)C.C[O:21][C:22](=O)/[CH:23]=[C:24](\[NH:26][C:27](=O)[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1)/[CH3:25]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:22](=[O:21])[CH:23]=[C:24]([CH3:25])[N:26]=[C:27]2[CH2:28][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27830553-Fluoro-4-(4-methylpiperazin-1-yl)anilineHCID 16682925TrimethylaluminumHCID 90022556Methyl 3-(2-(3-fluorophenoxy)acetamido)crotonate

Product 1

HCID 900516893-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-2-((3-fluorophenoxy)methyl)-6-methylpyrimidin-4(3H)-oneYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of 3-fluoro-4-(4-methylpiperazin-1-yl)aniline (0.63 g, 3.01 mmol) in DCM (15 mL) was added trimethylaluminium (5.3 mL, 10.6 mmol, 2 M in toluene) and the mixture was stirred at rt for 0.5 h. A solution of (Z)-methyl-3-(2-(3-fluorophenoxy)acetamido)but-2-enoate (0.80 g, 2.99 mmol) in DCM (5 mL) was added slowly and the resulting mixture was stirred at rt for 12 h. The mixture was then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (0.94 g, 73%). The compound was characterized by the following spectroscopic data:

Workup

  1. stirringthe resulting mixture was stirred at rt for 12 h
  2. customThe mixture was then quenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×2)
  4. washThe combined organic phases were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-17bdc8358cc8491caffa03c6788bfbb1
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434695B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes