Hydrochloric Acid → tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

HRID 1288385Notes

Reaction equation

HRID 1288385 reaction equation
[CH3:1][N:2]([CH2:15][CH2:16][CH:17]=[O:18])[C:3]([NH:5][C:6]1[S:7][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:9][N:10]=1)=[O:4].Cl>O>[C:11]([C:8]1[S:7][C:6]([N:5]2[CH:17]([OH:18])[CH2:16][CH2:15][N:2]([CH3:1])[C:3]2=[O:4])=[N:10][N:9]=1)([CH3:13])([CH3:14])[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 214000983-[1-Methyl(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Product 1

HCID 21400082tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 3-[1-methyl-3-(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde (16 grams), concentrated hydrochloric acid (10 ml) and water (500 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 filtered while hot and the filtrate is then cooled, resulting in the formation of a precipitate. The precipitate is recovered by filtration, dried and is recrystallized to yield the desired product tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-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 filtered while hot and the filtrate
  6. temperatureis then cooled
  7. customresulting in the formation of a precipitate
  8. filtrationThe precipitate is recovered by filtration
  9. customdried
  10. customis recrystallized

Sources & evidence

ORD record
ord-1f8b5a0bf9194da7b486cbdcd663c41b
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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