Hydrochloric Acid → HCID 178494687, compound

HRID 867885Notes

Reaction equation

HRID 867885 reaction equation
C([O:3][C:4](=O)[CH:5]([CH3:11])[C:6](=O)[CH2:7][O:8][CH3:9])C.C(O)(=O)C.[CH:17]([NH2:19])=[NH:18].C[O-].[Na+].[Na].Cl>CO.O>[CH3:9][O:8][CH2:7][C:6]1[C:5]([CH3:11])=[C:4]([OH:3])[N:19]=[CH:17][N:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 160693Formamidine acetateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 18315649Ethyl 4-methoxy-2-methyl-3-oxobutanoate

Product 1

HCID 178494687HCID 178494687, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

2-Methyl-3-keto-4-methoxybutyric acid ethyl ester (60 g) and formamidine acetate (39.06 g) were dissolved in methanol (150 ml) and treated, under nitrogen, with a sodium methoxide solution, prepared from sodium (17.42 g) and methanol (225 ml). The mixture was stirred at 50° for 23 hours, stripped, water added and the pH lowered to 7 (HCl). The solution was extracted with chloroform, extracts dried (MgSO4) and stripped to a residue, which was triturated with diethyl ether to give 4-methoxymethyl-5-methyl-6-hydroxypyrimidine, 38.72 g, m.p. 139°-140°.

Workup

  1. extractionThe solution was extracted with chloroform
  2. dry with materialextracts dried (MgSO4)
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-51ef9136c1ab445c92acdaa364afd0d0
Source dataset
uspto-grants-1988_10
Patent number
US04777172

Reaction notes

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