Ethyl cyanoformate → Ethyl 4-oxo-5-(2-thienyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate

HRID 606468Notes

Reaction equation

HRID 606468 reaction equation
[NH2:1][C:2]1[S:6][CH:5]=[C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[C:3]=1[C:12]([O:14]CC)=O.[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:18]>Cl.C(O)(=O)C>[O:14]=[C:12]1[NH:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:1][C:2]2[S:6][CH:5]=[C:4]([C:7]3[S:8][CH:9]=[CH:10][CH:11]=3)[C:3]1=2

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 718227Ethyl 2-amino-4-(thiophen-2-yl)thiophene-3-carboxylate

Product 1

HCID 59298332Ethyl 4-oxo-5-(2-thienyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylateYield 88.5%

Reagents, catalysts & solvents 1

HCID 22641269Acetate-hydrochloric acidSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 5′-amino-2,3′-bithiophene-4′-carboxylate (3.00 g, 11.842 mmol) was suspended in 1N hydrogen chloride-acetic acid solution (30 mL), ethyl cyanoformate (1.29 g, 13.026 mmol) was added, and the mixture was stirred under heating at 90° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The residue was suspended in diethyl ether, and the insoluble material was collected by filtration, washed with water to give the title compound as a brown powder (3.21 g, 88%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. filtrationthe insoluble material was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-db1da210e385403aa85d6be1a7fbe43e
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

Loading…