Sodium Hydroxide → 2-(4'-beta-Hydroxyethyl-piperazino)-5-oxo-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acid

HRID 66001Notes

Reaction equation

HRID 66001 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[CH:12][C:13]3[C:19](=[O:20])[C:18]([C:21]([O:23]CC)=[O:22])=[CH:17][N:16]([CH2:26][CH3:27])[C:14]=3[N:15]=2)[CH2:6][CH2:5]1.[OH-].[Na+]>C(O)(=O)C>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[CH:12][C:13]3[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:16]([CH2:26][CH3:27])[C:14]=3[N:15]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 227568342-(4'-beta-Hydroxyethyl-piperazino)-5-oxo-6-carbethoxy-8-ethylpyrido(2,3-d)pyrimidine

Product 1

HCID 128507632-(4'-beta-Hydroxyethyl-piperazino)-5-oxo-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acidYield 53.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.14 g. of the ester are added to an aqueous-alcoholic solution of sodium hydroxide (N NaOH: 15 cm3, ethanol: 10 cm3); the mixture is stirred for 2 hours at ordinary temperature and is then brought to pH 6 by adding acetic acid. After concentration to dryness in vacuo, the residue is taken up in a saturated solution of sodium acetate (50 cm3) and is extracted with chloroform (3 × 50 cm3). After drying (MgSO4), the solvent is evaporated and the residue is recrystallised from 80 cm3 of ethanol. 2.4 g. (53.3%) of 2-(4'-β-hydroxyethyl-piperazino)-5-oxo-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acid are obtained; melting point 222° C.

Workup

  1. concentrationAfter concentration to dryness in vacuo
  2. extractionis extracted with chloroform (3 × 50 cm3)
  3. dry with materialAfter drying (MgSO4)
  4. customthe solvent is evaporated
  5. customthe residue is recrystallised from 80 cm3 of ethanol

Sources & evidence

ORD record
ord-4db508f954184e3aab243dafe481e227
Source dataset
uspto-grants-1978_12
Patent number
US04129737

Reaction notes

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