Acetamidine monohydrochloride → HCID 178499609, compound

HRID 1728550Notes

Reaction equation

HRID 1728550 reaction equation
C([C:3](CC)([C:13]([O-:15])=[O:14])[C:4](CC)([C:8]([O-:10])=O)[C:5]([O-:7])=O)C.Cl.[C:19]([NH2:22])(=[NH:21])[CH3:20].[CH3:23][O-].[Na+]>CO>[OH:7][C:5]1[C:4]([CH2:3][C:13]([O:15][CH3:23])=[O:14])=[C:8]([OH:10])[N:22]=[C:19]([CH3:20])[N:21]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 45790110HCID 45790110, compound

Product 1

HCID 178499609HCID 178499609, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of triethyl-1,1,2-ethanetricarboxylate (20ml, 87mM) and acetamidine hydrochloride (8.22g, 87mM) was added to a solution of sodium methoxide (9.4g, 174mM) in dry methanol (100ml). The mixture was heated at 90° C. for 15 hours. The solvent was evaporated and the residue dissolved in water (150ml). The pH of the solution was adjusted to pH6 using concentrated hydrochloric acid. The resultant precipitate was collected by filtration, washed with water and then acetone, to give 4,6-dihydroxy-2-methylpyrimidine-5-acetic acid, methyl ester as a white solid (11.85g, 68.8%), m.p. >270° C.; microanalysis, found: C,48.5; H, 5.1; N, 14.1%; C7HSN204 requires C, 48.3; H,5.1; N, 13.8%; NMR: NaOD; 2.45(3H, s, pyrimidine-CH3), 3.57(2H,s,CH2), 3.87(3H,s,OCH3).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water (150ml)
  3. filtrationThe resultant precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-6f61294cbacb42278a95db4cc312bf4e
Source dataset
uspto-grants-1994_07
Patent number
US05328910

Reaction notes

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