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

HRID 50847

Reaction equation

HRID 50847 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>C(Cl)Cl>[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 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-aminothiophene-3-carboxylate (602.1 mg, 3.83 mmol) in formamide (5 mL) is heated at 200° C. for 12 h. The resulting tar is dissolved in CH2Cl2 (10 mL) then placed on a silica plug and eluted with 10% MeOH in CH2Cl2. The filtrate is stripped under reduce pressure and the resulting solid is washed with EtOH to yield 3H-thieno[2,3-d]pyrimid-4-one (231.4 mg, 40%) as an orange solid. 1H NMR (DMSO) δ 12.50 (1H, brs), 8.13 (1H, s), 7.60 (1H, d, J=5.8 Hz), 7.41 (1H, d, J=6.0 Hz).

Workup

  1. washeluted with 10% MeOH in CH2Cl2
  2. washthe resulting solid is washed with EtOH

Sources & evidence

ORD record
ord-ec81770f988643769db832e9958cef58
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Linked notes

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