Potassium Carbonate → methyl 2-[1-[(2'-cyanobiphenyl-4-yl)methyl]-6-ethyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl]propanoate

HRID 1889364Notes

Reaction equation

HRID 1889364 reaction equation
[CH2:1]([C:3]1[S:19][C:6]2[NH:7][C:8](=[O:18])[N:9]([CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:7]2[C:6]3[S:19][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=3[C:10](=[O:11])[N:9]([CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[C:8]2=[O:18])=[CH:27][CH:26]=1)#[N:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 59351712methyl 2-(6-ethyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)propanoate

Product 1

HCID 59351649methyl 2-[1-[(2'-cyanobiphenyl-4-yl)methyl]-6-ethyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl]propanoateYield 90.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-(6-ethyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)propanoate (9.9 g), 4′-(bromomethyl)biphenyl-2-carbonitrile (11.5 g), potassium carbonate (9.7 g) and acetonitrile (500 mL) was stirred at 50° C. for 2 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (15 g, 90%).

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cfaefe6a270f4d279141365452c6c1e4
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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