Diisopropylethylamine → HCID 11597749, compound

HRID 2267424Notes

Reaction equation

[CH2:1]([C:8]1[S:12][C:11]([C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[C:15](SC)[N:14]=2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OOS([O-])=O.[K+].[NH2:28][CH2:29][CH2:30][N:31]1[C:35]([CH3:37])([CH3:36])[C:34](=[O:38])[NH:33][C:32]1=[O:39].C(N(C(C)C)CC)(C)C>CC(C)=O.O.CC(O)C>[CH2:1]([C:8]1[S:12][C:11]([C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[C:15]([NH:28][CH2:29][CH2:30][N:31]3[C:35]([CH3:36])([CH3:37])[C:34](=[O:38])[NH:33][C:32]3=[O:39])[N:14]=2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 170 °C

Procedure

4-(5-Benzyl-1,3,4-thiadiazol-2-yl)-5-chloro-2-(methylthio)pyrimidine (0.190 g, 0.57 mmols) was dissolved in 75 mL acetone. Oxone (1.05 g, 1.7 mmol) was dissolved in 75 mL H2O and added to the acetone solution. This mixture was allowed to stir for 5 h. 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 (0.194 g, 1.1 mmol) and diisopropyl ethylamine (0.20 mL, 1.1 mmol) and 15 mL IPA. This reaction was heated under microwave conditions to 170° C. for 1200 s. Upon cooling 0.236 g (90% yield) of product was obtained by filtration. MS (M+H)+ 458.

Workup

customThe acetone was removed under vacuum
customthe resulting precipitate was obtained by filtration
customThis solid mixture was dried briefly in a vacuum oven

Sources & evidence

ORD record: ord-d885369461f64d04a7707449eaa69443
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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