Water → HCID 19071341, compound

HRID 1955618Notes

Reaction equation

HRID 1955618 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([S:13][CH3:14])[N:5]=[C:4]([CH3:15])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]([F:32])([F:31])[C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1.O>CN(C=O)C.[Cu](I)I>[CH3:15][C:4]1[N:5]=[C:6]([S:13][CH3:14])[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:2]([O:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:31])[F:32])[CH:25]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 19071337HCID 19071337, compound

Product 1

HCID 19071341HCID 19071341, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 2-(4-chloro-2-methyl-6-methylthio-pyrimidin-5-yl)-acetate (4.9 g) in DMF is added to a suspension of anhydrous potassium carbonate 5.6 g), copper iodide (1.0 g) and 3-trifluoromethylphenol (3.3 g) in DMF (50 ml) at room temperature. The mixture is heated to +120° C. for 90 minutes and then cooled. The cooled mixture is poured into water and extracted successively with ethyl acetate (2×50 ml) and then the organic phase is dried over anhydrous sodium sulfate. Evaporation and drying under high vacuum gives the methyl 2-[2-methyl-4-methylthio-6-(3-trifluoromethyl-phenoxy)-pyrimidin-5-yl]-acetate in form of a dark oil. NMR (CDCl3): 7.25-7.55 (m, 4H); 3.78 (s, 3H); 3.70 (s, 3H); 2.62 (s, 3H); 2.46 (s, 3H).

Workup

  1. temperatureThe mixture is heated to +120° C. for 90 minutes
  2. temperaturecooled
  3. extractionextracted successively with ethyl acetate (2×50 ml)
  4. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  5. customEvaporation
  6. customdrying under high vacuum

Sources & evidence

ORD record
ord-c16af4e9969b481b9b981ee1fdeb5d35
Source dataset
uspto-grants-1998_07
Patent number
US05776941

Reaction notes

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