N-methyl-2-pyrrolidone → 1-{2-[4-(5-Bromothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethylimidazolidine-2,4-dione

HRID 507575Notes

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].C(N(CC)C(C)C)(C)C.CN1CCCC1=O.[Br:29][C:30]1[S:34][C:33]([C:35]2[CH:40]=[CH:39][N:38]=[C:37](Cl)[N:36]=2)=[CH:32][CH:31]=1>CO.C1(C)C=CC=CC=1>[Br:29][C:30]1[S:34][C:33]([C:35]2[CH:40]=[CH:39][N:38]=[C:37]([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:36]=2)=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 180 °C

Procedure

1.22 mL (0.71 mmol) of a 10% (w/v) solution of 1-(2-aminoethyl)-5,5-dimethylimidazolidine-2,4-dione in MeOH was added to a 10 mL microwave vessel. The MeOH was evaporated with a stream of N2, to leave an oily solid which was dissolved in 0.34 mL (2.0 mmol) of N,N-diisopropylethylamine, 0.5 mL of N-methylpyrrolidinone and 3.5 mL of toluene, to which was added 0.15 g (0.65 mmol) of 4-(5-bromothiophen-2-yl)-2-chloropyrimidine. The reaction solution was heated in a microwave to 180° C. for 20 min then concentrated in vacuo and purified by flash chromatography eluting with a linear gradient of 75% EtOAc in hexane to neat EtOAc to deliver The title compound. MS (M+H)+ 410.

Workup

customThe MeOH was evaporated with a stream of N2
customto leave an oily solid which
concentrationthen concentrated in vacuo
custompurified by flash chromatography
washeluting with a linear gradient of 75% EtOAc in hexane to neat EtOAc

Sources & evidence

ORD record: ord-22e7755a138e498e99728daa33c7f622
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786132B2

Reaction notes

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