Acetic Acid → 7,8-Dihydro-1H-thiopyrano[3,2-d]pyrimidine-2,4(3H,6H)-dione

HRID 595071Notes

Reaction equation

HRID 595071 reaction equation
C(S[C:4]1[NH:5][C:6](=[O:14])[C:7]2[S:13][CH2:12][CH2:11][CH2:10][C:8]=2[N:9]=1)C.Cl.CC(O)=[O:18]>O>[NH:9]1[C:8]2[CH2:10][CH2:11][CH2:12][S:13][C:7]=2[C:6](=[O:14])[NH:5][C:4]1=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 135535910HCID 135535910, compound

Product 1

HCID 99899257,8-Dihydro-1H-thiopyrano[3,2-d]pyrimidine-2,4(3H,6H)-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2-(ethylthio)-7,8-dihydro-3H-thiopyrano[3,2-d]pyrimidin-4(6H)-one (4.5 g, 19.7 mmol) in water (20 mL) was added 3.0 mL of conc. HCl and 6.0 mL of AcOH. The mixture was heated to reflux and stirred overnight. The reaction was cooled and the solid that formed was collected by filtration, washed with water and methanol, evaporated and dried to obtain 7,8-dihydro-1H-thiopyrano[3,2-d]pyrimidine-2,4(3H,6H)-dione as a white solid (2.6 g, 72%). Without further purification, the crude product was used directly in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction was cooled
  4. customthe solid that formed
  5. filtrationwas collected by filtration
  6. washwashed with water and methanol
  7. customevaporated
  8. customdried

Sources & evidence

ORD record
ord-ed231be56d2f4202bd2a148f44cad9c0
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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