Diethyl Sulfate → Pipemidic Acid

HRID 1658120Notes

Reaction equation

HRID 1658120 reaction equation
[N:1]1([C:7]2[N:8]=[CH:9][C:10]3[C:16](=[O:17])[C:15]([C:18]([OH:20])=[O:19])=[CH:14][NH:13][C:11]=3[N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].S(OCC)(O[CH2:31][CH3:32])(=O)=O>C(O)(=O)C>[N:1]1([C:7]2[N:8]=[CH:9][C:10]3[C:16](=[O:17])[C:15]([C:18]([OH:20])=[O:19])=[CH:14][N:13]([CH2:31][CH3:32])[C:11]=3[N:12]=2)[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 10340Sodium CarbonateHCID 12850756HCID 12850756, compound

Product 1

HCID 4831Pipemidic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.5 g of 5,8-dihydro-2-(1-piperazinyl)- 5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid in 60 ml of a 10% aqueous solution of sodium carbonate was added three 10 ml portions of diethyl sulfate. After completion of the reaction, the resulting mixture was neutralized with acetic acid. The precipitate was collected and recrystallized from dimethylformamide to give 0.8 g of 2-(1-piperazinyl)-5,8-dihydro-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid (compound 1) m.p. 253° - 255°C. Concentration of the mother liquor to about a half volume gave another solid which was further recrystallized from the same solvent to give 0.6 g of 2-(4-ethyl-1-piperazinyl)-5,8-dihydro-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid (compound 21), m.p. 228° - 230°C.

Workup

  1. customAfter completion of the reaction
  2. customThe precipitate was collected
  3. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-af4840dc30cb449198e3957e51541302
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

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