Triethylamine → Ethyl 4-aminopyrimidine-2-carboxylate

HRID 2286673Notes

Reaction equation

HRID 2286673 reaction equation
Cl[C:2](=[CH2:5])[C:3]#[N:4].Br.[CH2:7]([O:9][C:10]([C:12]([NH2:14])=[NH:13])=[O:11])[CH3:8].C(N(CC)CC)C>C(O)C>[NH2:4][C:3]1[CH:2]=[CH:5][N:14]=[C:12]([C:10]([O:9][CH2:7][CH3:8])=[O:11])[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 233168511-Ethoxycarbonylformamidine hydrobromide

Product 1

HCID 13060222Ethyl 4-aminopyrimidine-2-carboxylateYield 57.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloroacrylonitrile(437 mg) and 1-ethoxycarbonylformamidine hydrobromide (985 mg) in ethanol (5 ml) was added dropwise triethylamine (1.01 g) at 0° C. The reaction mixture was stirred for 4 hours at ambient temperature and evaporated to dryness. The residue was dissolved in a mixture of ethyl acetate and water, and extracted with ethyl acetate three times. The combined extracts were dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was triturated with diethyl ether to give ethyl 4-aminopyrimidine-2-carboxylate (480 mg), which was recrystallized from a mixture of ethyl acetate and benzene, mp. 101°-104° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. extractionextracted with ethyl acetate three times
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-65919f36734d414f9dc68c1156a5c8d8
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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