Diisopropylethylamine → 1-(2-(5-Chloro-4-(5-(phenylamino)-1,3,4-thiadiazol-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 2267420Notes

Reaction equation

HRID 2267420 reaction equation
[Cl:1][C:2]1[C:3]([C:10]2[S:14][C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=3)=[N:12][N:11]=2)=[N:4][C:5](SC)=[N:6][CH:7]=1.OOS([O-])=O.[K+].[NH2:29][CH2:30][CH2:31][N:32]1[C:36]([CH3:38])([CH3:37])[C:35](=[O:39])[NH:34][C:33]1=[O:40].C(N(C(C)C)CC)(C)C>CC(C)=O.O.CC(O)C>[Cl:1][C:2]1[C:3]([C:10]2[S:14][C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][N:11]=2)=[N:4][C:5]([NH:29][CH2:30][CH2:31][N:32]2[C:36]([CH3:37])([CH3:38])[C:35](=[O:39])[NH:34][C:33]2=[O:40])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 23707502Potassium hydroxy sulfiteHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dioneHCID 602045505-(5-Chloro-2-(methylthio)pyrimidin-4-yl)-N-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 602045481-(2-(5-Chloro-4-(5-(phenylamino)-1,3,4-thiadiazol-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dioneYield 69.9%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

5-(5-Chloro-2-(methylthio)pyrimidin-4-yl)-N-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine (0.637 g, 1.7 mmol) was dissolved in 300 mL acetone. Oxone (6.3 g, 10.3 mmol) was dissolved in 300 mL H2O and added in one portion to the acetone solution and allowed to stir overnight at room temperature. The acetone was removed under vacuum, the resulting precipitate was obtained by filtration. LC/MS analysis indicates a mixture of both sulfoxide and sulfone. This solid mixture was dried briefly in a vacuum oven. This material was charged to a microwave reaction vessel along with 1-(2-aminoethyl)-5,5-dimethyl-imidazolidine-2,4-dione (0.588 g, 3.4 mmol), diisopropyl ethylamine (0.60 mL, 3.4 mmol) and 15 mL IPA. This reaction was heated under microwave conditions to 170° C. for 1200 s. Upon cooling 0.545 g (67% yield) of product was obtained by filtration. MS (M+H)+ 477.

Workup

  1. customThe acetone was removed under vacuum
  2. customthe resulting precipitate was obtained by filtration
  3. customThis solid mixture was dried briefly in a vacuum oven
  4. temperatureThis reaction was heated under microwave conditions to 170° C. for 1200 s

Sources & evidence

ORD record
ord-33ef8705095d43d29103e7f7aa594140
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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