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

HRID 1396781Notes

Reaction equation

HRID 1396781 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.O.[CH:12]([NH2:14])=O>>[N:1]1[C:2]2[S:3][CH:4]=[CH:5][C:6]=2[C:7](=[O:9])[NH:14][CH:12]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 78381Methyl 2-amino-3-thenoate

Product 1

HCID 2808547thieno(2,3-d)pyrimidin-4(3H)-oneYield 66%

Procedure

A solution of methyl 2-aminothiophene-3-carboxylate (3.0 g, 19.1 mmol) in formamide (95 ml) was heated at 190° C. for 4 hours. The cooled mixture was poured into water. The precipitate was filtered off, washed with water and dried. The crude product was purified by silica gel chromatography (CH2Cl2/MeOH 50:1) to yield the title compound as a white solid (1.93 g, 66%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried
  4. customThe crude product was purified by silica gel chromatography (CH2Cl2/MeOH 50:1)

Sources & evidence

ORD record
ord-59cf3e2cd6d54adca0f9d7b27db5fb34
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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