Acetamidine monohydrochloride → HCID 178433460, compound

HRID 868951Notes

Reaction equation

HRID 868951 reaction equation
CO[Na].Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].[CH3:9][CH:10]([C:15](OC)=[O:16])[C:11](OC)=[O:12]>CO>[CH3:6][C:5]1[N:8]=[C:11]([OH:12])[C:10]([CH3:9])=[C:15]([OH:16])[N:7]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 69104Dimethyl methylmalonateHCID 178418582HCID 178418582, compound

Product 1

HCID 178433460HCID 178433460, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of CH3ONa (5.02 g, 93 mmol) in CH3OH (31 mL) was cooled to 0° C. Acetamidine hydrochloride (3.21 g, 34 mmol) was added slowly. The reaction mixture was stirred at 0° C. for 30 min. Then dimethyl 2-methylmalonate (4.5 g, 31 mmol) was added. The mixture was stirred at 75° C. for 4 h, during which time a precipitate formed. The solid was filtered and dissolved in water and HCl (conc.) was added until pH 1-2. The white precipitate was filtered, and dried in vacuum to give 2,5-dimethylpyrimidine-4,6-diol as a white solid (3.41 g). MS (ESI): m/z 141 [M+H]+.

Workup

  1. stirringThe mixture was stirred at 75° C. for 4 h, during which time a precipitate
  2. customformed
  3. filtrationThe solid was filtered
  4. dissolutiondissolved in water
  5. additionHCl (conc.) was added until pH 1-2
  6. filtrationThe white precipitate was filtered
  7. customdried in vacuum

Sources & evidence

ORD record
ord-a95b7878762648a3a6a82c7b7a9f1460
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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