Urea → Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dione

HRID 2365154Notes

Reaction equation

HRID 2365154 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=O.[NH2:11][C:12](N)=[O:13]>>[NH:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:9])[NH:11][C:12]1=[O:13]

Participants

3

Reactant 2

HCID 1176UreaHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 7059273Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dione

Conditions

Temperature
190 °C

Procedure

A mixture of methyl 3-amino-2-thiophenecarboxylate (13.48 g, 85.85 mmol) and urea (29.75 g, 5 equivalents) was heated at 190° C. for 2 hours. The hot reaction mixture was then poured onto sodium hydroxide solution (2N, 300 mL) and any insoluble material removed by filtration. The mixture was then acidified to pH 6 by the addition concentrated HCl with cooling. The resultant white precipitate was collected by filtration and air dried (9.49 g, 66%).

Workup

  1. additionThe hot reaction mixture was then poured onto sodium hydroxide solution (2N, 300 mL)
  2. customany insoluble material removed by filtration
  3. additionThe mixture was then acidified to pH 6 by the addition concentrated HCl
  4. temperaturewith cooling
  5. filtrationThe resultant white precipitate was collected by filtration and air
  6. customdried (9.49 g, 66%)

Sources & evidence

ORD record
ord-0cb97a7c757a4360b3dfb0c9189348b1
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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