Ethanol → HCID 178477421, compound

HRID 2058156Notes

Reaction equation

HRID 2058156 reaction equation
S(O)(O)(=O)=O.C[NH:7][C:8](=[NH:11])[NH:9][CH3:10].[Na].C[O:14][C:15](=O)[CH2:16][C:17]([CH2:19][S:20][CH2:21][CH3:22])=O.[CH2:24](O)C>>[CH3:10][N:9]([CH3:24])[C:8]1[N:11]=[C:17]([CH2:19][S:20][CH2:21][CH3:22])[CH:16]=[C:15]([OH:14])[N:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 5360545SodiumHCID 14002634Methyl 4-(ethylthio)-3-oxobutanoateHCID 178485174HCID 178485174, compound

Product 1

HCID 178477421HCID 178477421, compound

Procedure

47.9 g of dimethylguanidine sulfate was added in portions, at room temperature, to a solution of 8.1 g of sodium in 300 ml of abs. ethanol. The mixture obtained was stirred for one hour at room temperature, and was subsequently refluxed for a further 30 minutes. After cooling, there was added dropwise 62.0 g of γ-ethylmercaptoacetoacetic acid methyl ester, and the resulting reaction mixture was refluxed for 24 hours. The reaction mixture obtained was cooled and subsequently poured into ice/water, and the pH was adjusted to 7. After extraction of the reaction mixture with methylene chloride, the organic phase was dried over Na2SO4 ; the solvent was then distilled off, and the resulting crude product was recrystallised from water to thus yield 2-dimethylamino-4-ethylmercaptomethyl-6-hydroxy-pyrimidine in the form of colourless crystals having a melting point of 119°-121° C.

Workup

  1. customThe mixture obtained
  2. temperaturewas subsequently refluxed for a further 30 minutes
  3. temperatureAfter cooling
  4. customthe resulting reaction mixture
  5. temperaturewas refluxed for 24 hours
  6. customThe reaction mixture obtained
  7. temperaturewas cooled
  8. extractionAfter extraction of the reaction mixture with methylene chloride
  9. dry with materialthe organic phase was dried over Na2SO4
  10. distillationthe solvent was then distilled off
  11. customthe resulting crude product was recrystallised from water to thus yield 2-dimethylamino-4-ethylmercaptomethyl-6-hydroxy-pyrimidine in the form of colourless crystals

Sources & evidence

ORD record
ord-a11ac29830c844c0a33c58fcb96d66d8
Source dataset
uspto-grants-1980_07
Patent number
US04215122

Reaction notes

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