Diisopropylethylamine → 1-(2-(5-Bromo-4-(thieno[2,3-c]pyridin-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 2267454Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:9]2[S:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:18][CH2:19][CH2:20][N:21]1[C:25]([CH3:27])([CH3:26])[C:24](=[O:28])[NH:23][C:22]1=[O:29].C(N(C(C)C)CC)(C)C>C(O)(C)C>[Br:1][C:2]1[C:3]([C:9]2[S:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=[N:4][C:5]([NH:18][CH2:19][CH2:20][N:21]2[C:25]([CH3:26])([CH3:27])[C:24](=[O:28])[NH:23][C:22]2=[O:29])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

2-(5-Bromo-2-chloropyrimidin-4-yl)thieno[2,3-c]pyridine (0.38 g, 1.16 mmol), 1-(2-aminoethyl)-5,5-dimethylimidazolidine-2,4-dione (0.393 g, 2.3 mmol), diisopropylethyl-amine (0.4 mL, 2.3 mmol) and isopropyl alcohol (2 mL) were all placed in a microwave tube and heated to 170° C. for 20 min. The volatiles were removed in vacuo and the residue dissolved in 9:1 mixture of dichloromethane, preadsorbed onto silica gel and purified by flash chromatography using a gradient of 0 to 10% methanol in dichloromethane to obtain a yellow solid. Yield=0.4 g. MS (M+H)+ 461/463.

Workup

customall placed in a microwave tube
customThe volatiles were removed in vacuo
dissolutionthe residue dissolved in 9:1 mixture of dichloromethane
custompurified by flash chromatography
customto obtain a yellow solid

Sources & evidence

ORD record: ord-25d14820cfcc4d858509282dddf2e4bc
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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