Chloranil → HCID 20256975, compound

HRID 637433Notes

Reaction equation

HRID 637433 reaction equation
C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C([O:15][C:16]([CH:18]1[CH2:33][N:32]([CH:34]2[CH2:36][CH2:35]2)[C:21]2[N:22]=[C:23]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[N:24]=[C:25]([CH3:26])[C:20]=2[C:19]1=[O:37])=[O:17])C>C1(C)C=CC=CC=1>[N:27]1([C:23]2[N:24]=[C:25]([CH3:26])[C:20]3[C:19](=[O:37])[C:18]([C:16]([OH:17])=[O:15])=[CH:33][N:32]([CH:34]4[CH2:36][CH2:35]4)[C:21]=3[N:22]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 54198532HCID 54198532, compound

Product 1

HCID 20256975HCID 20256975, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

100 ml of toluene and 2.5 g of chloranil are added to 3.4 g of 2-pyrrolidino-4-methyl-8-cyclopropyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester. The mixture is warmed at 80°-90° C. for 30 minutes, the solvent is stripped off in vacuo and the residue is recrystallised from acetonitrile. The resulting 2.2 g of the ester with a melting point of 170°-175° C. are heated with 20 ml of ethanol and a solution of 1.2 g of potassium hydroxide in 60 ml of H2O for 2.5 hours at the boil under reflux. The alcohol is distilled off, the filtered solution is acidified with glacial acetic acid and the precipitate is filtered off, washed with water and dried. 1.6 g of 2-pyrrolidino-4-methyl-8-cyclopropyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid with a melting point of 253° C. are obtained. (Example 2 (in Table 1)).

Workup

  1. temperatureThe mixture is warmed at 80°-90° C. for 30 minutes
  2. customthe residue is recrystallised from acetonitrile
  3. temperatureThe resulting 2.2 g of the ester with a melting point of 170°-175° C. are heated with 20 ml of ethanol
  4. temperaturea solution of 1.2 g of potassium hydroxide in 60 ml of H2O for 2.5 hours at the boil under reflux
  5. distillationThe alcohol is distilled off
  6. filtrationthe precipitate is filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-1f0e434942044c2189451631b585f19a
Source dataset
uspto-grants-1985_12
Patent number
US04556709

Reaction notes

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