Methanol → 1-{2-[4-(5-Benzyl-thiophen-2-yl)-pyrimidin-2-ylamino]-ethyl}-5,5-dimethyl-imidazolidine-2,4-dione

HRID 2267375Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[C:8]([CH3:10])([CH3:9])[C:7](=[O:11])[NH:6][C:5]1=[O:12].CO.C(N(CC)C(C)C)(C)C.[CH2:24]([C:31]1[S:35][C:34]([C:36]2[CH:41]=[CH:40][N:39]=[C:38](Cl)[N:37]=2)=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(O)C>[CH2:24]([C:31]1[S:35][C:34]([C:36]2[CH:41]=[CH:40][N:39]=[C:38]([NH:1][CH2:2][CH2:3][N:4]3[C:8]([CH3:9])([CH3:10])[C:7](=[O:11])[NH:6][C:5]3=[O:12])[N:37]=2)=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A 10% (w/v) solution of 1-(2-aminoethyl)-5,5-dimethylimidazolidine-2,4-dione in MeOH (0.93 mL, 0.54 mmol) was added to a 5 mL microwave vessel. The MeOH was evaporated with a stream of N2 to leave an oily solid which was dissolved in 94 μl (0.54 mmol) of N,N-diisopropylethylamine and 2 mL of iPrOH, to which was added 0.15 g (0.54 mmol) of 4-(5-benzylthiophen-2-yl)-2-chloropyrimidine. The reaction solution was heated in a microwave to 170° C. for 20 min and then allowed to stand at rt for 2 h to give a precipitate which was collected by filtration and purified by C-8 prep HPLC to give the title compound. MS (M+H)+ 422.

Workup

customThe MeOH was evaporated with a stream of N2
customto leave an oily solid which
customto give a precipitate which
filtrationwas collected by filtration
custompurified by C-8 prep HPLC

Sources & evidence

ORD record: ord-55eb8331ddf74220bdb5dbe82aa57fd3
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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