Hydrochloric Acid → tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone

HRID 1605881Notes

Reaction equation

HRID 1605881 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH:18]=[O:19])[C:5]([NH:7][C:8]1[S:9][C:10]([S:13]([CH3:15])=[O:14])=[N:11][N:12]=1)=[O:6])[C:2]#[CH:3].Cl>O>[CH3:15][S:13]([C:10]1[S:9][C:8]([N:7]2[CH:18]([OH:19])[CH2:17][CH2:16][N:4]([CH2:1][C:2]#[CH:3])[C:5]2=[O:6])=[N:12][N:11]=1)=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 214000753-[1-Propargyl-3-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Product 1

HCID 21400073tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 3-[1-propargyl-3-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde (15 grams), water (400 ml) and hydrochloric acid (4 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux for a period of about 15 minutes. The reaction mixture is then filtered while hot and the filtrate is cooled to form precipitate. The precipitate is recovered by filtration, is dried and is recrystallized to yield the desired product tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 15 minutes
  5. filtrationThe reaction mixture is then filtered while hot and the filtrate
  6. temperatureis cooled
  7. customto form precipitate
  8. filtrationThe precipitate is recovered by filtration
  9. customis dried
  10. customis recrystallized

Sources & evidence

ORD record
ord-1a7ee63b7ca64accab10cb63c01c5c40
Source dataset
uspto-grants-1976_04
Patent number
US03951976

Reaction notes

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