Ethyl 4-ethoxy-3-oxobutyrate → HCID 178467628, compound

HRID 1660478Notes

Reaction equation

HRID 1660478 reaction equation
C[O-].[Na+].Cl.[CH3:5][O:6][CH2:7][C:8]([NH2:10])=[NH:9].[CH2:11]([O:13][CH2:14][C:15](=O)[CH2:16][C:17](OCC)=[O:18])[CH3:12]>CO>[CH2:11]([O:13][CH2:14][C:15]1[N:10]=[C:8]([CH2:7][O:6][CH3:5])[N:9]=[C:17]([OH:18])[CH:16]=1)[CH3:12]

Participants

5

Reactant 3

HCID 3016245Ethyl 4-ethoxy-3-oxobutyrateHCID 10942334Sodium MethoxideHCID 135486022-Methoxyethanimidamide hydrochloride

Product 1

HCID 178467628HCID 178467628, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methylate (6.5 g, 0.12 mole) was added to a solution of methoxyacetamidine hydrochloride (6.23 g, 0.05 mole) and ethyl ethoxyacetoacetate (8.72 g. 0.05 mole) in methanol (50 ml) at room temperature, and the resulting white suspension liquor was stirred at 45° to 50° C. for 4 hours. The reaction mixture was treated in the same manner as in Example 5. Recrystallization from ether gave 8.5 g of 6-(ethoxymethyl)-4-hydroxy-2-(methoxymethyl)pyrimidine as white needle-like crystals (m.p. 96.5°-98° C.).

Workup

  1. additionThe reaction mixture was treated in the same manner as in Example 5
  2. customRecrystallization from ether

Sources & evidence

ORD record
ord-fb44222a5e0e45a78a7feb92095915a8
Source dataset
uspto-grants-1981_12
Patent number
US04308258

Reaction notes

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