Sodium ethoxide → Ethyl 2-(4-benzylpiperazino)-4-hydroxypyrimidine-5-acetate

HRID 570010Notes

Reaction equation

HRID 570010 reaction equation
[O-][CH2:2]C.[Na+].[Na].S(O)(O)(=O)=O.[C:11]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)(=[NH:13])[NH2:12].C([CH:29]([CH2:35][C:36]([O-:38])=O)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=O>C(O)C>[CH2:20]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[N:12]=[C:36]([OH:38])[C:35]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:2][N:13]=2)[CH2:15][CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfateHCID 5360545SodiumHCID 20146413Ethyl 2-formylsuccinate

Product 1

HCID 178470734Ethyl 2-(4-benzylpiperazino)-4-hydroxypyrimidine-5-acetateYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Added to an ethanol solution of sodium ethoxide, which had been prepared from 0.57 g (24.8 mmol) of sodium and 30 ml of EtOH, was 6.61 g (24.7 mmol) of 1-amidino-4-benzylpiperazine sulfate, followed by a dropwise addition of an ethanol solution (10 ml) of 5.0 g (24.7 mmol) of ethyl 2-formylsuccinate [the compound described in Ann. 363, 340] over 15 minutes. The resultant mixture was then refluxed for 4.5 hours. After cooling the reaction mixture, crystals were collected by filtration and then washed with water to obtain 3.65 g of the above-identified compound (yield: 41%).

Workup

  1. temperatureAfter cooling the reaction mixture, crystals
  2. filtrationwere collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-22fb9a57e25647d3b953a73612a98a58
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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