Acetic Acid → 6,7-Dihydrothieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

HRID 595058Notes

Reaction equation

HRID 595058 reaction equation
C(S[C:4]1[NH:5][C:6](=[O:13])[C:7]2[S:12][CH2:11][CH2:10][C:8]=2[N:9]=1)C.Cl.CC(O)=[O:17]>O>[NH:9]1[C:8]2[CH2:10][CH2:11][S:12][C:7]=2[C:6](=[O:13])[NH:5][C:4]1=[O:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 136096391HCID 136096391, compound

Product 1

HCID 444731766,7-Dihydrothieno[3,2-d]pyrimidine-2,4(1H,3H)-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 2-(ethylthio)-6,7-dihydrothieno[3,2-d]pyrimidin-4(3H)-one (2.80 g, 13.06 mmol) in water (2.0 mL) was added 2.0 mL of conc. HCl and 4.0 mL of AcOH. The mixture was heated at 110° C. overnight. The reaction was cooled and the solid that formed collected by filtration washed with water and methanol, and dried to afford a white solid, 6,7-dihydrothieno[3,2-d]pyrimidine-2,4(1H,3H)-dione, (1.80 g, 82%). Without further purification, the crude product was used directly to the next step.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solid that formed
  3. filtrationcollected by filtration
  4. washwashed with water and methanol
  5. customdried

Sources & evidence

ORD record
ord-bf3dd395102f463bb6416ea3b9e6b6ff
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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