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

HRID 888898Notes

Reaction equation

HRID 888898 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 (9.49g, 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 (9.49g, 66%)

Sources & evidence

ORD record
ord-2d54d1220dc446c89c1abf2a58a2a3fc
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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