Acetic Acid → 5,7-Dihydrothieno[3,4-d]pyrimidine-2,4-diol

HRID 595048Notes

Reaction equation

HRID 595048 reaction equation
C(S[C:4]1[NH:5][C:6](=[O:13])[C:7]2[CH2:12][S:11][CH2:10][C:8]=2[N:9]=1)C.Cl.CC(O)=[O:17]>O>[NH:9]1[C:8]2[CH2:10][S:11][CH2:12][C:7]=2[C:6](=[O:13])[NH:5][C:4]1=[O:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 135449010HCID 135449010, compound

Product 1

HCID 103521145,7-Dihydrothieno[3,4-d]pyrimidine-2,4-diolYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the suspension of 2-(ethylthio)thieno[3,4-d]pyrimidin-4-(3H, 5H, 7H)-one (2.88 g, 13.45 mmol) in water (20 mL) was added 2.0 mL of cone. HCl and 4.0 mL of AcOH. The reaction was heated at reflux overnight then cooled and the solid collected by filtration, washed with water and methanol, evaporated and dried to obtain a white solid thieno[3,4-d]pyrimidine-2,4-(1H, 3H, 5H, 7H)-dione (1.80 g, 80%). Without further purification, the crude product was used directly in the next step.

Workup

  1. additionwas added 2.0 mL of cone
  2. temperatureThe reaction was heated
  3. temperatureat reflux overnight
  4. temperaturethen cooled
  5. filtrationthe solid collected by filtration
  6. washwashed with water and methanol
  7. customevaporated
  8. customdried

Sources & evidence

ORD record
ord-e4e56741e6b54b6a9f8cb47a7dfc6b7f
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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