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

HRID 1415353Notes

Reaction equation

HRID 1415353 reaction equation
[CH3:1][N:2]([CH2:14][CH2:15][CH:16]=[O:17])[C:3]([NH:5][C:6]1[S:7][C:8]([CH:11]2[CH2:13][CH2:12]2)=[N:9][N:10]=1)=[O:4].Cl>O>[CH:11]1([C:8]2[S:7][C:6]([N:5]3[CH:16]([OH:17])[CH2:15][CH2:14][N:2]([CH3:1])[C:3]3=[O:4])=[N:10][N:9]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 214818963-[1-Methyl-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Product 1

HCID 21418670tetrahydro-1-(5-cyclopropyl-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-cyclopropyl-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-cyclopropyl-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 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-00df9a8749464b5085209c3281121b5e
Source dataset
uspto-grants-1977_01
Patent number
US04004912

Reaction notes

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