Chloroacetaldehyde → 5-(4-Hydroxybutylthio)imidazo[1,2-c]pyrimidine

HRID 357024Notes

Reaction equation

HRID 357024 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[N:3]=1.Cl[CH2:15][CH:16]=O>C(O)C>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][S:8][C:4]1[N:3]2[CH:15]=[CH:16][N:1]=[C:2]2[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 189368114-Amino-2-(4-hydroxybutylthio)pyrimidine

Product 1

HCID 189368825-(4-Hydroxybutylthio)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.98 g (25 mmol) of 4-amino-2-(4-hydroxybutylthio)pyrimidine in 70 ml of ethanol, 30 ml of a 40% chloroacetaldehyde solution was added, followed by refluxing for 4 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=1/1→1/4→ethyl acetate) to yield 3.15 g (56.4%, white crystal) of the desired product.

Workup

  1. temperatureby refluxing for 4 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=1/1→1/4→ethyl acetate)

Sources & evidence

ORD record
ord-b32d3089c842437fb6246ce71bf7e620
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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