Sodium Hydroxide → 2-(4-Benzylpiperazino)-6-ethyl-5-oxo-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 569991Notes

Reaction equation

HRID 569991 reaction equation
S(O)(O)(=O)=O.[C:6]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)(=[NH:8])[NH2:7].[OH-].[Na+].[CH2:24]([N:26]1[CH2:31][CH2:30][C:29](=O)[C:28](=[CH:33]OC)[C:27]1=[O:36])[CH3:25]>C(O)C>[CH2:15]([N:12]1[CH2:13][CH2:14][N:9]([C:6]2[N:7]=[CH:33][C:28]3[C:27](=[O:36])[N:26]([CH2:24][CH3:25])[CH2:31][CH2:30][C:29]=3[N:8]=2)[CH2:10][CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfateHCID 540921521-Ethyl-3-methoxymethylenepiperidine-2,4-dione

Product 1

HCID 137841212-(4-Benzylpiperazino)-6-ethyl-5-oxo-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidineYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension which had been obtained by adding 1.56 g of 1-amidino-4-benzylpiperazine sulfate to an ethanol solution of 0.23 g of sodium hydroxide, 1.07 g of 1-ethyl-3-methoxymethylenepiperidine-2,4-dione (Referential Example 37) was added. The resultant mixture was refluxed for 2 hours. After distilling off ethanol, water was added to the residue, followed by extraction with chloroform. After drying the chloroform layer, it was concentrated to obtain 1.4 g of 2-(4-benzylpiperazino)-6-ethyl-5-oxo-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (yield: 69%).

Workup

  1. customTo a suspension which had been obtained
  2. additionwas added
  3. distillationAfter distilling off ethanol, water
  4. additionwas added to the residue
  5. extractionfollowed by extraction with chloroform
  6. dry with materialAfter drying the chloroform layer, it
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-9801a83f8e1a42d89eafa66ceaa379e3
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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