Triethyl phosphite → Methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin-4-yloxymethyl) phenyl]acrylate

HRID 991170Notes

Reaction equation

HRID 991170 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].P(OCC)(OCC)OCC.[CH3:26][O:27][CH:28]=[C:29]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40]Br)[C:30]([O:32][CH3:33])=[O:31].COC=C(C1C=CC=CC=1CN1C(=O)C=C(C(F)(F)F)N=C1OC(C)C)C(OC)=O>CCCCCCCC.[Cu-]=O.CC(C)=O.O>[CH3:26][O:27][CH:28]=[C:29]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][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:30]([O:32][CH3:33])=[O:31]

Participants

9

Reactant 4

HCID 31215Triethyl phosphiteHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 69904693Methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin4-on-3-ylmethyl)phenyl]acrylateHCID 178458952HCID 178458952, compound

Product 1

HCID 53395020Methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin-4-yloxymethyl) phenyl]acrylate

Reagents, catalysts & solvents 4

HCID 178419072HCID 178419072, compoundCatalystHCID 180AcetoneSolventHCID 356OctaneSolvent2×HCID 962WaterSolvent3×

Procedure

2.22 g of 2-isopropoxy-6-trifluoromethyl-4-hydroxypyrimidine and 0.72 g of copper(I) oxide were suspended in 50 ml of octane. The suspension was refluxed until no water was recognized to form, while formed water was being taken into a quantitative water receiver. 1.66 g of triethyl phosphite was added, and, 30 minutes later, 2.41 g of methyl 3-methoxy-2-(2-bromomethylphenyl)acrylate was added at an instance. The reaction was carried out for 20 hours at reflux of octane. The solution was cooled down to room temperature. 20 ml of acetone was added to it. Insoluble matter was filtrated, and further washed with 10 ml of acetone twice. The mixed solution of the obtained filtrate and washings was analyzed with high-performance liquid chromatography. Yields were 66.4% for the target compound, and as for byproducts 1.4% for methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin4-on-3-ylmethyl)phenyl]acrylate and 17.4% for 4-( α-methoxy)methylen-2H-chromen-3(4H)-one.

Workup

  1. customto form
  2. filtrationInsoluble matter was filtrated
  3. washfurther washed with 10 ml of acetone twice
  4. customYields

Sources & evidence

ORD record
ord-a610c157f3e74e29845857ea88601cf4
Source dataset
uspto-grants-2002_10
Patent number
US06462195B1

Reaction notes

Loading…