Dimethyl acetylenedicarboxylate → HCID 12285744, compound

HRID 1912473Notes

Reaction equation

HRID 1912473 reaction equation
[NH2:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10]([C:16]([O:18][CH3:19])=[O:17])#[C:11][C:12]([O:14][CH3:15])=[O:13]>CO>[O:8]=[C:5]1[NH:4][C:3](=[O:9])[C:2]([NH:1]/[C:11](=[CH:10]/[C:16]([O:18][CH3:19])=[O:17])/[C:12]([O:14][CH3:15])=[O:13])=[CH:7][NH:6]1

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 136115-Aminouracil

Product 1

HCID 12285744HCID 12285744, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-aminouracil (275 g, 2.16 mol) in dry methanol (5.5 L) was added dropwise dimethyl acetylene dicarboxylate (344 g, 2.42 mol) at room temperature. After the end of the addition, the mixture was stirred at room temperature for 24 hours. The precipitate was filtered off, washed with MeOH (500 mL) and dried under vacuum to afford the title compound (430 g, 74%) as a yellow solid.

Workup

  1. additionAfter the end of the addition
  2. filtrationThe precipitate was filtered off
  3. washwashed with MeOH (500 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-392d3486eeb84758bf87f514547be83e
Source dataset
uspto-grants-2013_12
Patent number
US08609666B2

Reaction notes

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