Formamide → thieno(2,3-d)pyrimidin-4(3H)-one

HRID 335253

Reaction equation

HRID 335253 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.[CH:11]([NH2:13])=O>O>[N:1]1[C:2]2[S:3][CH:4]=[CH:5][C:6]=2[C:7](=[O:9])[NH:13][CH:11]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 78381Methyl 2-amino-3-thenoate

Product 1

HCID 2808547thieno(2,3-d)pyrimidin-4(3H)-oneYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

Methyl 2-aminothiophene-3-carboxylate (10 g, 64 mmol) was charged with formamide (50 mL). The reaction was heated at 190° C. under nitrogen for 3 hours. The solution was cooled to room temperature. The slurry was poured into 125 mL of water and extracted with chloroform:isopropyl alcohol mixture (2 times). The solution was concentrated and triturated to afford the title compound (2.25 g, 23%).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with chloroform
  3. concentrationThe solution was concentrated
  4. customtriturated

Sources & evidence

ORD record
ord-5deb13959e074614875884ddb94d098d
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Linked notes

Loading…