Dimethyl Sulfate → HCID 21270710, compound

HRID 1193888Notes

Reaction equation

HRID 1193888 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[C:19]([F:22])=[C:18]([C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[NH:17][C:16]2=[O:30])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[C:31](=O)(O)[O-].[Na+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[C:19]([F:22])=[C:18]([C:23]([F:28])([F:29])[C:24]([F:25])([F:26])[F:27])[N:17]=[C:16]2[O:30][CH3:31])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:8])[CH3:9])=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 21270753HCID 21270753, compound

Product 1

HCID 21270710HCID 21270710, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9.2 g of crude isopropyl 2-chloro-5-[3,6-dihydro-2,6-dioxo-5-fluoro-4-pentafluoroethyl -1(2H) -pyrimidinyl]-4-fluorobenzoate, 3.36 g of sodium bicarbonate and 3.78 g of dimethyl sulphate in 50 ml of anhydrous acetone is heated to reflux temperature for 3 hours. After cooling the solid constituents are filtered off under suction and the filtrate is evaporated to dryness under reduced pressure. The residue is separated by chromatography on a silica gel column using n-hexane/diethyl ether (2:1). There is obtained isopropyl 2-chloro-4-fluoro-5-[5-fluoro-2-methoxy-6-oxo-4-pentafluoroethyl -1(6H)-pyrimidinyl]-benzoate, m.p. 75°-77° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature for 3 hours
  3. temperatureAfter cooling the solid constituents
  4. filtrationare filtered off under suction
  5. customthe filtrate is evaporated to dryness under reduced pressure
  6. customThe residue is separated by chromatography on a silica gel column

Sources & evidence

ORD record
ord-c2d8ff0c13ca47748c60dfdca5b3eafe
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

Loading…