Hydrochloric Acid → HCID 86746705, compound

HRID 1590282Notes

Reaction equation

HRID 1590282 reaction equation
COC1NC(C)=C(C(OCC)=O)C(C2C=CC=C(Cl)C=2Cl)N=1.N1C=CC=CC=1.ClC(OCC)=O.Cl.[CH3:36][C:37]1[NH:38][C:39](=[O:61])[N:40]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH:41]([C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[C:49]=2[Cl:55])[C:42]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44]>ClCCl.O1CCCC1CO>[CH3:36][CH:37]1[C:42]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:41]([C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[C:49]=2[Cl:55])[N:40]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[C:39](=[O:61])[NH:38]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 13975861HCID 13975861, compoundHCID 86746706HCID 86746706, compound

Product 1

HCID 86746705HCID 86746705, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(2,3-dichlorophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (1.3 g., 3.8 mmole) in dichloromethane (10 ml.) is cooled to 0° and treated with pyridine (0.6 ml., 7.58 mmole) followed by ethyl chloroformate (0.4 ml., 4.0 mmole). The cooling bath is removed and the reaction is allowed to stir at room temperature overnight. The solvent is then stripped off to provide a colorless solid. This material is dissolved in tetrahydrofuran-methanol (10 ml. of 1:4 mixture) and treated with 2N hydrochloric acid (2 ml.). The reaction is allowed to stir at room temperature for 30 minutes and the solvent is then evaporated. The residue is extracted with ethyl acetate and the combined extracts are washed with sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent is stripped and the residue is crystallized from isopropyl ether to provide 1.25 g. of 3,6-dihydro-4-methyl-6-(2,3-dichlorophenyl)-2-oxo-1,5(2H)pyrimidinedicarboxylic acid, diethyl ester as a colorless solid; m.p. 139.5°-141°. TLC(silica gel; acetone/hexanes, 50:50) Rf =0.44.

Workup

  1. customThe cooling bath is removed
  2. customto provide a colorless solid
  3. stirringto stir at room temperature for 30 minutes
  4. customthe solvent is then evaporated
  5. extractionThe residue is extracted with ethyl acetate
  6. washthe combined extracts are washed with sodium bicarbonate and brine
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. customthe residue is crystallized from isopropyl ether
  9. customto provide 1.25 g

Sources & evidence

ORD record
ord-03db73418db24cadb431cee639f50d21
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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