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

HRID 2267298Notes

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-98c6b33efee447a789b16c7151476ab6
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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