Dimethyl Sulfoxide → 4'-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1889366노트

반응식

HRID 1889366 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C:13]1[S:42][C:16]2[N:17]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:30][CH:29]=3)[C:18](=[O:26])[N:19]([CH:22]([CH3:25])[CH2:23][OH:24])[C:20](=[O:21])[C:15]=2[CH:14]=1)[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([C:13]1[S:42][C:16]2[N:17]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:30][CH:29]=3)[C:18](=[O:26])[N:19]([CH:22]([CH3:25])[CH:23]=[O:24])[C:20](=[O:21])[C:15]=2[CH:14]=1)[CH3:12]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 593516824'-{[6-ethyl-3-(2-hydroxy-1-methylethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

생성물 1

HCID 593515604'-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile수율 85.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a mixture of oxalylchloride (0.43 mL) and methylene chloride (10 mL) were added a solution (10 mL) of dimethyl sulfoxide (0.35 mL) in methylene chloride and a solution (10 mL) of 4′-{[6-ethyl-3-(2-hydroxy-1-methylethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (2 g) in methylene chloride at −78° C., and the mixture was stirred at the same temperature for 15 min. Triethylamine (3.14 mL) was added, and the mixture was allowed to warm to room temperature. The reaction mixture was washed with water and 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 colorless amorphous solid (1.7 g, 85%).

후처리

  1. washThe reaction mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6dc8ccf46b1941e89bcb40b83b066e1f
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501750B2

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