Acetamidine monohydrochloride → HCID 178432745, compound

HRID 1682540Notes

Reaction equation

HRID 1682540 reaction equation
[C:1]([CH:4]([CH2:9][C:10]([O:12]C)=[O:11])[C:5]([O:7]C)=O)(=O)[CH3:2].C[O-].[Na+].CO.Cl.[C:20]([NH2:23])(=[NH:22])[CH3:21]>>[CH3:21][C:20]1[N:23]=[C:5]([OH:7])[C:4]([CH2:9][C:10]([OH:12])=[O:11])=[C:1]([CH3:2])[N:22]=1

Participants

4

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 112039Dimethyl acetylsuccinateHCID 23694274Sodium methanolate methanol

Product 1

HCID 178432745HCID 178432745, compoundYield 93.3%

Procedure

Dimethyl acetylsuccinate (188 g, 1 mol) is dissolved in sodiummethylate/methanol (1.1 mol in 500 ml) and added within 30 minutes to a solution of acetamidine hydrochloride (104 g, 1.1 mol) at 60° C. with stirring. After refluxing the mixture for 14 hours, the precipitated salt is removed by filtration and the filtrate is evaporated to dryness under reduced pressure. The resulting solid is suspended in acetone, filtered and dried to give (2,6-dimethyl-4-hydroxy-5-pyrimidinyl) acetic acid crystalline product (170 g, 93%). 1H-NMR (DMSO):12.3 (s, 1H); 3.2 (s, 2H); 2.2. (s, 3H); 2.1 (s, 3H).

Workup

  1. temperatureAfter refluxing the mixture for 14 hours
  2. customthe precipitated salt is removed by filtration
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-771bd66f106746eabf6bd9d35c6ca03e
Source dataset
uspto-grants-1997_06
Patent number
US05635508

Reaction notes

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