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

HRID 66003Notes

Reaction equation

HRID 66003 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[CH:16][C:17]3[C:23](=[O:24])[C:22]([C:25]([O:27]CC)=[O:26])=[CH:21][N:20]([CH2:30][CH3:31])[C:18]=3[N:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]=[CH:16][C:17]3[C:23](=[O:24])[C:22]([C:25]([OH:27])=[O:26])=[CH:21][N:20]([CH2:30][CH3:31])[C:18]=3[N:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 122668082-(4'-Benzyl-piperazino)-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine

Product 1

HCID 122668192-(4'-Benzyl-piperazino)-5-oxo-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acid

Procedure

Saponification of 9.5 g. of this ester with an aqueous-alcoholic solution of sodium hydroxide (N NaOH, 15 cm3 + water, 30 cm3 + ethanol, 30 cm3) is complete in 1 hour at ordinary temperature. After acidification, the precipitate is filtered off and recrystallised from 160 cm3 of a mixture of dimethylformamide (1 volume) and ethanol (1 volume). 6.8 g. of 2-(4'-benzyl-piperazino)-5-oxo-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acid are obtained; melting point 207° C.

Workup

  1. filtrationAfter acidification, the precipitate is filtered off
  2. customrecrystallised from 160 cm3 of a mixture of dimethylformamide (1 volume) and ethanol (1 volume)

Sources & evidence

ORD record
ord-0c2072622429402ea8774467ed573bfa
Source dataset
uspto-grants-1978_12
Patent number
US04129737

Reaction notes

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