Ethyl 4-oxotetrahydrothiophene-3-carboxylate → HCID 178517924, compound

HRID 625047Notes

Reaction equation

HRID 625047 reaction equation
Cl.[CH:2]([NH2:4])=[NH:3].CC[O-].[Na+].O=[C:10]1[CH2:14][S:13][CH2:12][CH:11]1[C:15](OCC)=[O:16]>C(O)C>[N:3]1[C:10]2[CH2:14][S:13][CH2:12][C:11]=2[C:15]([OH:16])=[N:4][CH:2]=1

Participants

5

Reactant 3

HCID 310629Ethyl 4-oxotetrahydrothiophene-3-carboxylateHCID 2723922Sodium ethoxideHCID 10313058Methanimidamide, hydrochloride (1:1)

Product 1

HCID 178517924HCID 178517924, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of formamidine HCl salt (3.70 g, 46.0 mmol) in ethanol (200 mL) was added NaOEt in ethanol (21% wt, 17.2 mL, 46.0 mmol). The mixture was stirred at room temperature for 1 hour. The ethyl 4-oxotetrahydrothiophene-3-carboxylate (8.0 g, 46.0 mmol) was added. The mixture was stirred at room temperature for 4 hours and then refluxed overnight. After cooling, the solvent was removed and the residue was washed with a small amount of water and CH2Cl2 to afford 5,7-dihydrothieno[3,4-d]pyrimidin-4-ol as light brown solid (2.5 g, 35%). 1H NMR (d6-DMSO, 400 MHz) δ 12.59 (s, 1H), 8.13 (s, 1H), 4.12 (s, 2H), 3.96 (s, 2H). MS (APCI+) [M+H]+ 155.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. temperaturerefluxed overnight
  3. temperatureAfter cooling
  4. customthe solvent was removed
  5. washthe residue was washed with a small amount of water and CH2Cl2

Sources & evidence

ORD record
ord-ac2e5559dae045218539af9dd5365531
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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