Ethanol → 5,8-Dihydro-2-(1-piperazinyl)-8-vinyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid hydrochloride

HRID 1658139Notes

Reaction equation

HRID 1658139 reaction equation
C(O)C.[H-].[Na+].C([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:16]=[CH:17][C:18]3[C:24](=[O:25])[C:23]([C:26]([O:28]CC)=[O:27])=[CH:22][N:21]([CH2:31][CH2:32][Cl:33])[C:19]=3[N:20]=2)[CH2:11][CH2:10]1)(=O)C>O>[ClH:33].[N:12]1([C:15]2[N:16]=[CH:17][C:18]3[C:24](=[O:25])[C:23]([C:26]([OH:28])=[O:27])=[CH:22][N:21]([CH:31]=[CH2:32])[C:19]=3[N:20]=2)[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 13334740Ethyl 2-(4-acetyl-1-piperazinyl)-8-(2-chloroethyl)-5,8-dihydro-5-oxopyrido[2,3-d]-pyrimidine-6-carboxylate

Product 1

HCID 123790215,8-Dihydro-2-(1-piperazinyl)-8-vinyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid hydrochlorideYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture, containing 400 ml of absolute ethanol and 2.0 g of 65% sodium hydride, which was held at 60°C was added with stirring 5.0 g of ethyl 2-(4-acetyl-1-piperazinyl)-8-(2-chloroethyl)-5,8-dihydro-5oxopyrido[2,3-d]pyrimidine-6-carboxylate. The resulting mixture was heated to reflux for 2 hours and at the end of the period 200 ml of water was added. The mixture was refluxed for an additional 30 minutes. The ethanol was distilled off under reduced pressure and the resulting residue was acidified with concentrated hydrochloric acid to pH 1.0. The resulting precipitate was collected and recrystallized from water to yield 2.8 g of the product, m.p 298° - 301°C with decomposition.

Workup

  1. customwas held at 60°C
  2. additionwas added
  3. temperatureThe resulting mixture was heated
  4. additionwas added
  5. temperatureThe mixture was refluxed for an additional 30 minutes
  6. distillationThe ethanol was distilled off under reduced pressure
  7. customThe resulting precipitate was collected
  8. customrecrystallized from water

Sources & evidence

ORD record
ord-1b693982a9d841e2850a56eb795798c4
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

Loading…