Water → Methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin-4-yloxymethyl) phenyl]acrylate
Reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([OH:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[N:6]=1)([CH3:3])[CH3:2].O.[CH3:17][O:18][CH:19]=[C:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Br)[C:21]([O:23][CH3:24])=[O:22].COC=C(C1C=CC=CC=1CON1C(=O)C=C(C(F)(F)F)N=C1OC(C)C)C(OC)=O>C1(C)C=CC=CC=1.[Cu-]=O>[CH3:17][O:18][CH:19]=[C:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][O:11][C:9]1[CH:8]=[C:7]([C:12]([F:14])([F:15])[F:13])[N:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[N:10]=1)[C:21]([O:23][CH3:24])=[O:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2.22 g of 2-isopropoxy-6-trifluoromethyl-4-hydroxypyrimidine and 0.72 g of copper(I) oxide were suspended in 30 ml of toluene. The suspension was refluxed until no water was recognized to form, while formed water was being taken into a quantitative water receiver. 3.08 g of methyl 3-methoxy-2-(2-bromomethylphenyl)acrylate was added at an instance. The reaction was carried out for 5 hours at reflux of toluene. Then the solution was cooled down to room temperature. Insoluble matter was filtrated and further washed with 20 ml of acetone twice. The mixed solution of the obtained filtrate and washings was analyzed with high-performance liquid chromatography. The reaction yield was 22.3% and as for byproducts 0.7% for methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin-4-on-3-yloxymethyl)phenyl]acrylate and 77% for 4-(α-methoxy) methylen-2H-chromen-3(4H)-one.
Workup
- customto form
- filtrationInsoluble matter was filtrated
- washfurther washed with 20 ml of acetone twice
- customThe reaction yield was 22.3%
Sources & evidence
- ORD record
- ord-0871534c1e5e473f922cd5abec815cd5
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06462195B1
Reaction notes
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