Sodium → Methyl 4-aminopyrimidine-2-carboxylate

HRID 1075274Notes

Reaction equation

HRID 1075274 reaction equation
Cl.C(O[CH:5]=[CH:6][C:7](=[NH:11])OCC)C.Br.[CH2:13]([O:15][C:16]([C:18]([NH2:20])=[NH:19])=[O:17])C.[Na]>CO>[NH2:11][C:7]1[CH:6]=[CH:5][N:20]=[C:18]([C:16]([O:15][CH3:13])=[O:17])[N:19]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 233168511-Ethoxycarbonylformamidine hydrobromideHCID 86737728Ethyl 3-ethoxyacrylimidate hydrochloride

Product 1

HCID 13060221Methyl 4-aminopyrimidine-2-carboxylateYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of ethyl 3-ethoxyacrylimidate hydrochloride (4.0 g) and 1-ethoxycarbonylformamidine hydrobromide (4.4 g) in methanol (110 ml) was added dropwise a solution of sodium metal (1 g) in methanol (110 ml) at 0° C. The reaction mixture was stirred for an hour at 0° to 5° C. and for additional 4 hours at ambient temperature. The solution was evaporated to dryness and the residue was dissolved in a mixture of ethyl acetate and an aqueous solution of sodium chloride. The organic layer was separated out and the aqueous layer was extracted with ethyl acetate five times. All organic layers were combined, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was triturated with diethylether to give methyl 4-aminopyrimidine-2-carboxylate (1.33 g), which was recrystallized from ethyl acetate, mp. 140°-142.5° C.

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate
  3. customThe organic layer was separated out
  4. extractionthe aqueous layer was extracted with ethyl acetate five times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was triturated with diethylether

Sources & evidence

ORD record
ord-4a85533222bf44bc8f533d8887f71f67
Source dataset
uspto-grants-1983_07
Patent number
US04395411

Reaction notes

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