Water → 1-Methylethyl 2-chloro-4-fluoro-5-(2-methoxy-6-oxo-4-(pentafluoroethyl)-1(6H)-pyrimidinyl)benzoate

HRID 1193890Notes

Reaction equation

HRID 1193890 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[NH:17][C:16]2=[O:29])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[H-].[Na+].S(OC)(O[CH3:36])(=O)=O.O>CN(C)C=O>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:27])([F:28])[C:23]([F:25])([F:26])[F:24])[N:17]=[C:16]2[O:29][CH3:36])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:8])[CH3:9])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 21270707HCID 21270707, compound

Product 1

HCID 1354011-Methylethyl 2-chloro-4-fluoro-5-(2-methoxy-6-oxo-4-(pentafluoroethyl)-1(6H)-pyrimidinyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.51 g of isopropyl 2-chloro-5-[3,6-dihydro-2,6-dioxo-4-pentafluoroethyl -1(2H)-pyrimidinyl ]-4-fluorobenzoate are added at room temperature while stirring to a suspension of 0.93 g of a 55% sodium hydride dispersion in 25 ml of dimethylformamide and the mixture is stirred at room temperature for 30 minutes. The mixture is subsequently treated with 4.04 g of dimethyl sulphate and stirred at 50° C. for 4 hours. The reaction mixture is cooled and poured into 500 ml of water, and the aqueous solution is extracted twice with 100 ml of ethyl acetate each time. The organic phase is washed twice with 100 ml of water each time, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is separated by chromotography on a silica el column using n-hexane/diethyl ether (2:1) as the eluent. The product is recrystallized from n-hexane. There is obtained isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-pentafluoroethyl -1(6H)-pyrimidinyl]-benzoate, m.p. 82°-84° C.

Workup

  1. stirringstirred at 50° C. for 4 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionthe aqueous solution is extracted twice with 100 ml of ethyl acetate each time
  4. washThe organic phase is washed twice with 100 ml of water each time
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is separated by chromotography on a silica el column
  8. customThe product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-9356d80a8bd34361b8ece73cb0fe8ba0
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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