Triethylamine → 1-(2-(4-(Benzo[b]thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

HRID 507532Notes

Reaction equation

[S:1]1[C:5]([C:6]2[CH:11]=[CH:10][N:9]=[C:8](S(C)(=O)=O)[N:7]=2)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.[NH2:20][CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][NH:25][C:24]1=[O:28].C(N(CC)CC)C>COC(O)C>[S:1]1[C:5]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][NH:25][C:24]3=[O:28])[N:7]=2)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(benzo[b]thiophen-2-yl)-2-(methylsulfonyl)pyrimidine (75 mg, 0.26 mmol)), 1-(2-aminoethyl)imidazolidin-2-one (33 mg, 0.26 mmol) and triethylamine (32 mg, 0.31 mmol) in methoxyethanol (3 mL) was heated at 100° C. overnight. After cooling to rt the solvent was removed in vacuo and the product was purified by chromatography eluting with methanol/dichloromethane (1:20) to give the title compound as a slightly yellow solid (56 mg, 64%). MS (M+H)+ 340.

Workup

temperatureAfter cooling to rt the solvent
customwas removed in vacuo
customthe product was purified by chromatography
washeluting with methanol/dichloromethane (1:20)

Sources & evidence

ORD record: ord-72932030c4064bb58a23803b89e4bfa8
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786132B2

Reaction notes

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