2-Amino-4,6-dimethyl pyrimidine → HCID 13488534, compound

HRID 637871

Reaction equation

HRID 637871 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22]([N:25]=[C:26]=[S:27])(=[O:24])=[O:23])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[C:16]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:17]([S:22]([NH:25][C:26]([NH:1][C:2]2[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=2)=[S:27])(=[O:23])=[O:24])=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 134220272-Phenylbenzenesulfonyl isothiocyanate

Product 1

HCID 13488534HCID 13488534, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

77 g of potassium N-(2-biphenylylsulfonyl)carbonimidodithioate prepared in accordance with Example 2 was suspended in 100 ml of toluene, and 37 ml of thionyl chloride was added to the suspension at 0° to 10° C. over the course of 1 hour. After the addition, the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. Distillation at reduced pressure gave 2-phenylbenzenesulfonyl isothiocyanate. On the other hand, 12.3 g of 2-amino-4,6-dimethylpyrimidine was suspended in 300 ml of dry toluene, and 27.5 g of 2-phenylbenzenesulfonyl isothiocyanate prepared as above was added. The mixture was heated under reduced pressure for 8 hours. After cooling, the resulting white precipitate was collected by filtration, and recrystallized from ethanol to give 31 g of the desired 1-(2-biphenylsulfonyl)3-(4,6-dimethylpyrimidin-2-yl)thiourea of the following formula, mp. 203°-204° C.: ##STR20##

Workup

  1. additionas above was added
  2. temperatureThe mixture was heated under reduced pressure for 8 hours
  3. temperatureAfter cooling
  4. filtrationthe resulting white precipitate was collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-57c6e18292f84d52a6e378771ccbe330
Source dataset
uspto-grants-1985_12
Patent number
US04559079

Linked notes

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