2-Methylbenzenesulfonic acid → tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-butoxy-2(1H)-pyrimidinone

HRID 1288375Notes

Reaction equation

HRID 1288375 reaction equation
[CH3:1][S:2]([C:5]1[S:9][C:8]([N:10]2[CH:15]([OH:16])[CH2:14][CH2:13][N:12]([CH2:17][CH:18]=[CH2:19])[C:11]2=[O:20])=[N:7][N:6]=1)(=[O:4])=[O:3].[C:21]1(C)[C:22](S(O)(=O)=O)=CC=[CH:25][CH:26]=1>C(O)CCC>[CH3:1][S:2]([C:5]1[S:9][C:8]([N:10]2[CH:15]([O:16][CH2:22][CH2:21][CH2:26][CH3:25])[CH2:14][CH2:13][N:12]([CH2:17][CH:18]=[CH2:19])[C:11]2=[O:20])=[N:7][N:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 21400079Tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21501671tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-butoxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-hydroxy-2(1H)-pyrimidinone (7 grams), butyl alcohol (50 ml) and toluenesulfonic acid (0.2 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is then heated at reflux for a period of about 24 hours. After this time the mixture is stripped of unreacted alcohol under reduced pressure to yield a solid product. This product is then recrystallized to yield the desired product tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-butoxy-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is then heated
  4. temperatureat reflux for a period of about 24 hours
  5. customto yield a solid product
  6. customThis product is then recrystallized

Sources & evidence

ORD record
ord-70909a285b964aa7bc5888306bf6f230
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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