3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester → 5,7-Dihydrothieno[3,4-d]pyrimidin-4-ol

HRID 45146

Reaction equation

HRID 45146 reaction equation
[C:1]([CH:5]1[CH2:9][S:8][CH2:7][C:6]1=O)(OC)=[O:2].C(O)(=O)C.[CH:15]([NH2:17])=[NH:16].[O-]CC.[Na+]>CCO>[N:16]1[C:6]2[CH2:7][S:8][CH2:9][C:5]=2[C:1](=[O:2])[NH:17][CH:15]=1

Participants

5

Reactant 3

HCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 160693Formamidine acetateHCID 2723922Sodium ethoxide

Product 1

HCID 1360263465,7-Dihydrothieno[3,4-d]pyrimidin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Commercially available 4-carbomethoxytetrahydro-3-thiophenone (5 g, 31.2 mmol) is dissolved in EtOH (284 mL). Formamidine acetate (22 g, 211 mmol) is then added followed by sodium ethoxide (45 mL, 121 mmol, 21% w/w) and the mixture is heated at 90° C. for 14 hours. Reaction is cooled to room temperature and concentrated to a residue which is absorbed onto silica and separated via FCC (0-10% Methanol:CH2Cl2) to give the title compound as a solid. MS (ESI) m/z 155.14 (M+1).

Workup

  1. customReaction
  2. temperatureis cooled to room temperature
  3. concentrationconcentrated to a residue which
  4. customis absorbed onto silica
  5. customseparated via FCC (0-10% Methanol:CH2Cl2)

Sources & evidence

ORD record
ord-c65ef26a23c34fcbbc5714fcf01e5d96
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Linked notes

Loading…