Potassium Carbonate → 3'-bromo-4'-{[3-(2,4-dimethoxybenzyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1889429Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:4]=1[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([CH2:16][CH3:17])[S:15][C:9]=2[NH:8][C:7]1=[O:18].[Br:25][C:26]1[CH:27]=[C:28]([C:34]2[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:29]=[CH:30][C:31]=1[CH2:32]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:25][C:26]1[CH:27]=[C:28]([C:34]2[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:29]=[CH:30][C:31]=1[CH2:32][N:8]1[C:9]2[S:15][C:14]([CH2:16][CH3:17])=[CH:13][C:10]=2[C:11](=[O:12])[N:6]([CH2:5][C:4]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:3]=2[O:2][CH3:1])[C:7]1=[O:18]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-(2,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (3.4 g), 3′-bromo-4′-(bromomethyl)biphenyl-2-carbonitrile (3.8 g), potassium carbonate (2.7 g) and acetonitrile (200 mL) was stirred at 50° C. for 2 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (4.92 g, 81%).

Workup

filtrationInsoluble material was filtered off
customthe solvent was evaporated under reduced pressure
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-d95b627820364b0b8346a01502883fda
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501750B2

Reaction notes

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