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

HRID 1288378Notes

Reaction equation

HRID 1288378 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 a 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 a precipitate
  8. filtrationThe precipitate is recovered by filtration
  9. customis dried
  10. customis recrystallized

Sources & evidence

ORD record
ord-81e8cb3c73264f8a89d326745a09e71c
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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