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Sodium Hydroxide → Methyl 2-(4-benzylpiperazino)-4-methylpyrimidine-5-carboxylate

HRID 569979
Notes
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Reaction equation

HRID 569979 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[C:8]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)(=[NH:10])[NH2:9].CO[CH:26]=[C:27]([C:32]([CH3:34])=O)[C:28]([O:30][CH3:31])=[O:29]>CO>[CH2:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[N:9]=[C:32]([CH3:34])[C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][N:10]=2)[CH2:12][CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfateHCID 54260517Methyl alpha-methoxymethyleneacetoacetate

Product 1

HCID 13784088Methyl 2-(4-benzylpiperazino)-4-methylpyrimidine-5-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

One hundred milliliters of a 1M solution of sodium hydroxide in methanol were added to a suspension (60 ml) of 26.8 g (0.1 mol) of 1-amidino-4-benzylpiperazine sulfate [which had been synthesized in accordance with the process disclosed in J. Am. Chem. Soc., 66, 263 (1944)] in methanol, followed by a dropwise addition of 15.8 g (0.1 mol) of methyl α-methoxymethyleneacetoacetate. After stirring the resultant mixture overnight at room temperature, the precipitated sodium sulfate was filtered off. After distilling off methanol, the residue was dissolved in 500 ml of ethyl acetate. The resultant solution was washed twice with 100 ml of water. The ethyl acetate layer was washed with saturated saline and then dried with anhydrous magnesium sulfate. Upon distilling off ethyl acetate, 28.7 g of the intended compound was obtained as an orange-colored oily substance (yield: 88%). When the oily substance was left over at room temperature subsequent to its distillation under a reduced pressure, it was crystallized.

Workup

  1. customhad been synthesized in accordance with the process
  2. filtrationthe precipitated sodium sulfate was filtered off
  3. distillationAfter distilling off methanol
  4. dissolutionthe residue was dissolved in 500 ml of ethyl acetate
  5. washThe resultant solution was washed twice with 100 ml of water
  6. washThe ethyl acetate layer was washed with saturated saline
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationUpon distilling off ethyl acetate

Sources & evidence

ORD record
ord-82ae2132712e4ca1b57edef47a5e8dd9
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04734418

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes