Diethyl Sulfate → HCID 23042369, compound

HRID 2165803Notes

Reaction equation

HRID 2165803 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:18]2=[O:28])=[CH:12][C:3]=1[C:4]([O:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5].C(=O)(O)[O-].[K+].S(OCC)(O[CH2:38][CH3:39])(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[N:19]([CH2:38][CH3:39])[C:18]2=[O:28])=[CH:12][C:3]=1[C:4]([O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:5]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 516893Potassium BicarbonateHCID 23042372HCID 23042372, compound

Product 1

HCID 23042369HCID 23042369, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.5 g of cyclopentyl 2-chloro-5-[3.6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate, 2.1 g of potassium bicarbonate and 1.5 ml of diethyl sulphate are heated at reflux temperature in 50 ml of acetone for 4 hours. Subsequently. the solvent is distilled off and the residue is partitioned in 150 ml of diethyl ether and 150 ml of water. The aqueous phase is extracted with a further 150 ml of diethyl ether and the combined organic phases are washed twice with 150 ml of water each time, dried over anhydrous magnesium sulphate and concentrated. The residue is purified by chromatography on a silica gel column using ethyl acetate/n-hexane (1:4) as the eluent. In this manner there are obtained cyclopentyl 2-chloro-5-[3-ethyl-3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate as a colourless oil, 1H-NMR (CDCl 3, 400 MHz : 1 36 (t3H), 1.56-2.04 (m,8H), 4.02 (q,2H), 5.36-5.45 (m,1H), 6.35 (s,1H), 7.36 (d,1H), 7.82 (d,1H); mass spectrum (m/e): M+ 448 (1), as well as cyclopentyl 2-chloro- 5-[2-ethoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-fluorobenzoate, m.p. 90°-91° C.

Workup

  1. distillationthe solvent is distilled off
  2. customthe residue is partitioned in 150 ml of diethyl ether
  3. extractionThe aqueous phase is extracted with a further 150 ml of diethyl ether
  4. washthe combined organic phases are washed twice with 150 ml of water each time
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-59b1db57fefa47bdafbf7aac7d20032c
Source dataset
uspto-grants-1990_07
Patent number
US04941909

Reaction notes

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