Acetic Acid → 2-Mercapto-5,6-dimethylthieno[2,3-d]pyrimidin-4(3h)-one

HRID 711647Notes

Reaction equation

HRID 711647 reaction equation
[CH3:1][C:2]1[C:3]([C:12]([O:14]CC)=O)=[C:4]([NH:8][C:9]([NH2:11])=[S:10])[S:5][C:6]=1[CH3:7].[OH-].[Na+].CC(O)=O>CCO>[CH3:1][C:2]1[C:3]2[C:12](=[O:14])[NH:11][C:9](=[S:10])[NH:8][C:4]=2[S:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 777992Ethyl 2-(carbamothioylamino)-4,5-dimethylthiophene-3-carboxylate

Product 1

HCID 7600402-Mercapto-5,6-dimethylthieno[2,3-d]pyrimidin-4(3h)-oneYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl 4,5-dimethyl-2-thioureidothiophene-3-carboxylate (Example 50a) (37 mg, 0.17 mmol) in dry EtOH (10 mL) was added sodium hydroxide (21 mg, 0.52 mmol). The reaction mixture was then stirred at room temperature for 5 minutes and refluxed for 10 minutes. The reaction mixture was cooled to room temperature, neutralized with 10% AcOH and then concentrated to dryness. The residue was purified by chromatography on silica gel (Gradient 0-50% EtOAc in Hexanes) to give the title compound (8 mg) in 24% yield. 1H NMR (400 MHz, DMSO-d6) δ 2.25 (s, 6H), 12.24 (s, 1H), 13.27 (s, 1H). MS 202 (MH+).

Workup

  1. temperaturerefluxed for 10 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by chromatography on silica gel (Gradient 0-50% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-6c25b6a4351f40dd98fe245ebc575e68
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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