2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 2,6-dimethyl-3-(2-(4-morpholinophenyl)thiazol-5-yl)pyrimidin-4(3H)-one
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[S:14][C:15]([NH2:18])=[CH:16][N:17]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C[Al](C)C.[NH:23](/[C:27](/[CH3:33])=[CH:28]\[C:29](OC)=[O:30])[C:24]([CH3:26])=O>C(Cl)Cl>[CH3:26][C:24]1[N:18]([C:15]2[S:14][C:13]([C:10]3[CH:9]=[CH:8][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:12][CH:11]=3)=[N:17][CH:16]=2)[C:29](=[O:30])[CH:28]=[C:27]([CH3:33])[N:23]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(4-morpholinophenyl)thiazol-5-amine (0.20 g, 0.77 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (2.3 mL, 4.6 mmol, 2 M in toluene) dropwise at rt. The reaction mixture was stirred at rt for 1 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (132 mg, 0.84 mmol) in anhydrous CH2Cl2 (5 mL). The reaction mixture was stirred at rt overnight, 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 preparative TLC to give the title compound as a pale yellow solid (20 mg, 7%). The compound was characterized by the following spectroscopic data:
Workup
- stirringThe reaction mixture was stirred at rt overnight
- 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 preparative TLC
Sources & evidence
- ORD record
- ord-0893ecf08c374e40a862e51ea95e6d11
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
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