HCID 178498315, compound → HCID 15052081, compound

HRID 2351266Notes

Reaction equation

HRID 2351266 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[N:3]=1>C(O)(=O)C.C(Cl)(Cl)Cl.[Zn]>[O:1]=[C:2]1[NH:3][C:4]([C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:6]([C:8]([O:10][CH3:11])=[O:9])[NH:7]1

Participants

5

Reactant 1

HCID 178498315HCID 178498315, compound

Product 1

HCID 15052081HCID 15052081, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst3×HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Dimethyl 2-hydroxypyrimidine-4,6-dicarboxylate (1.0 g. 4.7 mmol) was dissolved in warm acetic acid (17M. 70 ml) and heated to 70°. Zinc dust (1.5 g. 22.9 mmol) was added to this stirred solution portionwise over a period of 1 h. Each addition of a zinc portion was accompanied by a purple colour change of the reaction mixture. This colour slowly dissipated, then further zinc was added in similar fashion until completion. The resulting mixture was stirred at 70° for 30 min. The reaction mixture was filtered and washed with acetic acid (17M, 2×10 ml). The filtrate was evaporated to dryness under reduced pressure to give a colourless oil. The residual oil was dissolved in chloroform (100 ml), filtered and the solvent removed to give colourless crystals. The crude product was recrystallized from methanol to give dimethyl 2-oxo-1,2,3,6-tetrahydropyrimidine-4,6-dicarboxylate as colourless prisms, (283 mg. 28%) m.p. 177°-179°

Workup

  1. temperatureheated to 70°
  2. filtrationThe reaction mixture was filtered
  3. washwashed with acetic acid (17M, 2×10 ml)
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. customto give a colourless oil
  6. filtrationfiltered
  7. customthe solvent removed
  8. customto give colourless crystals
  9. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-9a207a08e75b4b5a9b15685b72b5685b
Source dataset
uspto-grants-1989_10
Patent number
US04873228

Reaction notes

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