Pyridine → tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-cyclopropylthiocarbonyloxy-2(1H)-pyrimidinone

HRID 441473Notes

Reaction equation

HRID 441473 reaction equation
[CH3:1][S:2]([C:4]1[S:8][C:7]([N:9]2[CH:14]([OH:15])[CH2:13][CH2:12][N:11]([CH2:16][C:17]#[CH:18])[C:10]2=[O:19])=[N:6][N:5]=1)=[O:3].ClC(OC1CC1)=[S:22].N1[CH:32]=[CH:31][CH:30]=[CH:29]C=1>>[CH3:1][S:2]([C:4]1[S:8][C:7]([N:9]2[CH:14]([O:15][C:29]([CH:30]3[CH2:32][CH2:31]3)=[S:22])[CH2:13][CH2:12][N:11]([CH2:16][C:17]#[CH:18])[C:10]2=[O:19])=[N:6][N:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 1049Pyridine2×HCID 21400073tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinoneHCID 54242527Cyclopropyl chlorothioformate

Product 1

HCID 53922020tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-cyclopropylthiocarbonyloxy-2(1H)-pyrimidinone

Procedure

Tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone (0.05 mole) dissolved in pyridine (80 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The solution is cooled to a temperature of about 10° C. and cyclopropyl chlorothioformate (0.06 mole) dissolved in pyridine (25 ml) is slowly added with stirring over a period of about 15 minutes. After the addition is completed, the reaction mixture is warmed to room temperature and is stirred for an additional period of about 20 minutes to ensure completion of the reaction. After this time the reaction mixture is filtered. The filtrate is then combined with water (100 ml) resulting in the formation of a precipitate. This precipitate is recovered by filtration and is dissolved in ether. The ether solution is washed with dilute aqueous sodium carbonate, is dried over anhydrous magnesium sulfate and is filtered. The filtrate is then stripped of ether to yield the desired product tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-cyclopropylthiocarbonyloxy-2(1H)-pyrimidinone as the residue. EXAMPLE 48

Workup

  1. additionis charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. additionis slowly added
  4. additionAfter the addition
  5. stirringis stirred for an additional period of about 20 minutes
  6. customcompletion of the reaction
  7. filtrationAfter this time the reaction mixture is filtered
  8. customresulting in the formation of a precipitate
  9. filtrationThis precipitate is recovered by filtration
  10. dissolutionis dissolved in ether
  11. washThe ether solution is washed with dilute aqueous sodium carbonate
  12. dry with materialis dried over anhydrous magnesium sulfate
  13. filtrationis filtered

Sources & evidence

ORD record
ord-06e6c17093144755bff1f88b301a8ba8
Source dataset
uspto-grants-1977_08
Patent number
US04040812

Reaction notes

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