Dimethylformamide → HCID 59351832, compound

HRID 1889382Notes

Reaction equation

HRID 1889382 reaction equation
[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8](=[O:12])[NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[C:29]12([C:39](=[O:42])[CH2:40]Br)[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2.CN(C)C=O.[H-].[Na+]>C(OCC)(=O)C>[C:29]12([C:39](=[O:42])[CH2:40][N:9]3[C:10](=[O:11])[C:5]4[CH:4]=[C:3]([CH2:1][CH3:2])[S:28][C:6]=4[N:7]([CH2:13][C:14]4[CH:19]=[CH:18][C:17]([C:20]5[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=5)=[CH:16][CH:15]=4)[C:8]3=[O:12])[CH2:36][CH:35]3[CH2:34][CH:33]([CH2:32][CH:31]([CH2:37]3)[CH2:30]1)[CH2:38]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketoneHCID 593517704'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 59351832HCID 59351832, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4′-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile (1.0 g), 1-(1-adamantyl)-2-bromoethanone (1.0 g) and N,N-dimethylformamide (8 mL) was added 60% sodium hydride (0.16 g), and the mixture was stirred at room temperature for 24 hr. The reaction mixture was diluted with ethyl acetate, successively washed with water and saturated brine and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.68 g, 47%).

Workup

  1. washsuccessively washed with water and saturated brine
  2. dry with materialsaturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-be616668d97c4acb836659deb3662f9d
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

Loading…