Sodium Chloride → 3-Amino-2-imino-6-methyl-2,3-dihydropyrimidin-4(1H)-one

HRID 591221Notes

Reaction equation

HRID 591221 reaction equation
CC[O-].[Na+].[Na].[C:6]([NH:9][NH2:10])([NH2:8])=[NH:7].Cl.[Na+].[Cl-].O=[C:15]([CH3:22])[CH2:16][C:17](OCC)=[O:18]>C(O)C>[NH2:7][C:6]1[N:9]([NH2:10])[C:17](=[O:18])[CH:16]=[C:15]([CH3:22])[N:8]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8868Ethyl AcetoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 178418668HCID 178418668, compound

Product 1

HCID 9131753-Amino-2-imino-6-methyl-2,3-dihydropyrimidin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of NaOEt prepared from sodium (FLUKA, 9.19 g, 400 mmol) and ethanol (350 mL) was added aminoguanidine hydrochloride (ALDRICH, 44.2 g, 400 mmol). The reaction mixture was heated at 50° C. for 30 min. Then, the mixture was filtered to remove NaCl, and ethyl 3-oxobutanoate (ALDRICH, 25.3 mL, 200 mmol) was added to the filtrate. The reaction mixture was heated under reflux for 5 h and, then, stirred at room temperature overnight. The precipitate obtained was filtered and dried under vacuum to afford Intermediate 1 as a pale pink solid.

Workup

  1. filtrationThen, the mixture was filtered
  2. additionwas added to the filtrate
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 5 h
  5. customThe precipitate obtained
  6. filtrationwas filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-14cd1255a38d4f75999a61648930ba35
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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