Boron trifluoride etherate → HCID 178467437, compound

HRID 1390308Notes

Reaction equation

HRID 1390308 reaction equation
[Cl:1][C:2]1[C:3](C(OCC)=O)=[N:4][CH:5]=[N:6][CH:7]=1.ClC1[C:15]([C:20]([OH:22])=O)=NC=NC=1.B(F)(F)F.C[CH2:28][O:29]CC.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)C>[Cl:1][C:2]1[C:3]([O:22][CH2:20][CH3:15])=[N:4][C:5](=[C:28]=[O:29])[NH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium Bicarbonate2×HCID 200293965-Chloropyrimidine-4-carboxylic acidHCID 21329182Ethyl 5-chloropyrimidine-4-carboxylate

Product 1

HCID 178467437HCID 178467437, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-Chloro-4-ethoxycarbonylpyrimidine can be prepared by treating 5-chloro-4-carboxypyrimidine (40 g) with ethanol (400 cc) and boron trifluoride etherate (80 cc). After heating for 24 hours under reflux, the volatile materials are eliminated and then methylene chloride (250 cc) is added. An 8% (w/v) aqueous sodium bicarbonate solution (100 cc) is added and then the pH is adjusted to 6 by the addition of sodium bicarbonate powder. A further extraction is carried out with methylene chloride (300 cc). The solvent is evaporated off and then the residue distilled. 5-Chloro-4-ethoxy-carbonylpyrimidine (23 g), b.p. 132°-133° C./33 mm Hg, is obtained.

Workup

  1. temperatureAfter heating for 24 hours
  2. temperatureunder reflux
  3. extractionA further extraction
  4. customThe solvent is evaporated off
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-0ac7c64a8a164223beb0a6a87a27de1a
Source dataset
uspto-grants-1979_02
Patent number
US04138487

Reaction notes

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