Hydrochloric Acid → HCID 178494551, compound

HRID 1863207Notes

Reaction equation

HRID 1863207 reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].[CH3:9][O:10][C:11](=O)[CH2:12][C:13]([CH2:15][O:16]C)=O.Cl>CO>[CH3:6][C:5]1[N:8]=[C:12]([CH2:11][O:10][CH3:9])[CH:13]=[C:15]([OH:16])[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67170Acetamidine monohydrochlorideHCID 123500Methyl 4-methoxyacetoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 178494551HCID 178494551, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

968 g (4 mol) of sodium methylate in methanol were added to a solution of 187 g (2 mol) of acetamidine hydrochloride and 292 g (2 mol) of γ-methoxyacetoacetic acid methyl ester in 1,000 ml of methanol at 5° C., the mixture was warmed for 3 hours at 50° C. and the solvent was then stripped off under reduced pressure. The residue was dissolved in 500 ml of ice-water and brought to pH ca.6 with concentrated hydrochloric acid, while cooling externally, the precipitate was filtered off, washed with ether and then dried in a desiccator over phosphorus pentoxide. 180 g (58% of theory) of 2-methyl-4-methoxymethyl-6-hydroxy-pyrimidine were obtained in the form of a white powder of melting point 168°-170° C.

Workup

  1. temperaturewhile cooling externally
  2. filtrationthe precipitate was filtered off
  3. washwashed with ether
  4. dry with materialdried in a desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-631d2f1a573548d59eff290fec0c34a1
Source dataset
uspto-grants-1979_09
Patent number
US04168304

Reaction notes

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