2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(4-(bis(2-propoxyethyl)amino)-3-fluorophenyl)-2,6-dimethyl pyrimidin-4(3H)-one
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15].C[Al](C)C.[NH:26](/[C:30](/[CH3:36])=[CH:31]\[C:32](OC)=[O:33])[C:27]([CH3:29])=O>C(Cl)Cl>[CH2:13]([O:12][CH2:11][CH2:10][N:9]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH3:21])[C:3]1[CH:4]=[CH:5][C:6]([N:8]2[C:32](=[O:33])[CH:31]=[C:30]([CH3:36])[N:26]=[C:27]2[CH3:29])=[CH:7][C:2]=1[F:1])[CH2:14][CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-fluoro-N1,N1-bis(2-propoxyethyl)benzene-1,4-diamine (0.50 g, 1.68 mmol) in CH2Cl2 (10 mL) was added trimethylaluminum (3.4 mL, 6.8 mmol, 2 M in toluene) slowly. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (0.32 g, 2.02 mmol) in CH2Cl2 (2 mL). The reaction mixture was stirred at rt for 72 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as pale yellow oil (0.53 g, 78%). The compound was characterized by the following spectroscopic data:
Workup
- stirringThe reaction mixture was stirred at rt for 72 h
- customquenched with saturated NH4Cl aqueous solution
- extractionextracted with CH2Cl2 (50 mL×3)
- dry with materialThe combined organic phases were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)
Sources & evidence
- ORD record
- ord-7c3b65d676664db99dc9b02695df5e4e
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
Loading…