Triethylamine → 4-Amino-2-(3-ethoxycarbonylpropylthio)pyrimidine

HRID 357022Notes

Reaction equation

HRID 357022 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[S:12].C(N(CC)CC)C>C(O)C>[NH2:15][C:14]1[CH:16]=[CH:17][N:10]=[C:11]([S:12][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76300Ethyl 4-bromobutyrateHCID 178507915HCID 178507915, compound

Product 1

HCID 189367844-Amino-2-(3-ethoxycarbonylpropylthio)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen atmosphere, 28.6 ml (200 mmol) of ethyl 4-bromobutyrate was added to a solution of 25.44 g (200 mmol) of 2-thiocytosine and 30.7 ml (220 mmol) of triethylamine in 400 ml of ethanol at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→1/9) to yield 46.31 g (96.0%, white crystal) of the desired product.

Workup

  1. temperatureby refluxing for 16 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→1/9)

Sources & evidence

ORD record
ord-ec17460d8faa4527be035f34a7cc30c0
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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