Sodium Carbonate → 1-(2-(4-(5-(4-Methoxyphenyl)thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

HRID 507523Notes

Reaction equation

Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][NH:18][C:17]3=[O:21])[N:8]=2)=[CH:4][CH:3]=1.C([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)C.[C:33](=O)([O-])[O-:34].[Na+].[Na+]>COCCOC>[CH3:33][O:34][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[S:6][C:5]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][N:16]4[CH2:20][CH2:19][NH:18][C:17]4=[O:21])[N:8]=3)=[CH:4][CH:3]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-(2-(4-(5-bromothiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one (30 mg, 0.08 mmol), 4-ethylphenylboronic acid (16 mg, 0.1 mmol), tetrakis(triphenyl-phosphine)palladium (9 mg, 0.008 mmol) and 2 M sodium carbonate (0.08 mL, 0.16 mmol) in 1,2-dimethoxyethane (3 mL) was heated at 150° C. for 25 min in a Personal Chemistry microwave reactor. Upon cooling, the mixture was filtered through celite and washed with ethyl acetate. Solvent was removed under vacuum and the product was purified by column chromatography eluting with MeOH/CH2Cl2 (1:20) to yield a slight yellow solid (18, mg, 56%). MS (M+H)+ 396.

Workup

temperatureUpon cooling
filtrationthe mixture was filtered through celite
washwashed with ethyl acetate
customSolvent was removed under vacuum
customthe product was purified by column chromatography
washeluting with MeOH/CH2Cl2 (1:20)
customto yield a slight yellow solid (18, mg, 56%)

Sources & evidence

ORD record: ord-9b48d64690db4f29b17f50d1936c3087
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786132B2

Reaction notes

Loading…