2-(4'-Benzyl-piperazino)-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine → Ethyl 8-Ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate (Pipemidic Acid Ethyl Ester)

HRID 1658136Notes

Reaction equation

HRID 1658136 reaction equation
C([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][CH2:28][CH3:29])=[O:26])=[CH:21][N:20]([CH2:30][CH3:31])[C:18]=3[N:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C>[CH2:30]([N:20]1[C:18]2[N:19]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]=[CH:16][C:17]=2[C:23](=[O:24])[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21]1)[CH3:31]

Participants

3

Reactant 1

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

Product 1

HCID 12266832Ethyl 8-Ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate (Pipemidic Acid Ethyl Ester)Yield 106%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.0 g of ethyl 2-(4-benzyl-1-piperazinyl)-5,8-dihydro-8-ethyl-5-oxopyrido[2,3-d]-pyrimidine-6-carboxylate in 100 ml of ethanol was allowed to consume an equivalent amount of hydrogen over 1.5 g of 10% palladium-on-carbon under hydrogen atmosphere. The reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated to give a solid which was collected and recrystallized from acetone. There is obtained 2.5 g of the product, m.p. 156° - 158°C.

Workup

  1. customto consume an equivalent amount of hydrogen over 1.5 g of 10% palladium-on-carbon under hydrogen atmosphere
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated
  5. customto give a solid which
  6. customwas collected
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-aa0b8b46d0794ae9a9f7c536767c8095
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

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