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

HRID 1889359ノート

反応式

HRID 1889359 の反応式
Br[C:2]1[CH:3]=[C:4]([C:10](=[O:40])[CH2:11][N:12]2[C:17](=[O:18])[C:16]3[CH:19]=[C:20]([CH2:22][CH3:23])[S:21][C:15]=3[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=4)=[CH:27][CH:26]=3)[C:13]2=[O:39])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:41]B(O)O.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH2:22]([C:20]1[S:21][C:15]2[N:14]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]4[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=4)=[CH:29][CH:30]=3)[C:13](=[O:39])[N:12]([CH2:11][C:10]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([CH3:41])[CH:3]=3)=[O:40])[C:17](=[O:18])[C:16]=2[CH:19]=1)[CH3:23]

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 593516184'-{[3-[2-(3-bromo-4-methoxyphenyl)-2-oxoethyl]-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

生成物 1

HCID 593516474'-{[6-ethyl-3-[2-(4-methoxy-3-methylphenyl)-2-oxoethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile収率 81%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A mixture of 4′-{[3-[2-(3-bromo-4-methoxyphenyl)-2-oxoethyl]-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (1.3 g), methylboronic acid (0.25 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (0.086 g), potassium carbonate (0.88 g), tetrahydrofuran (50 mL) and water (5 mL) was stirred under argon atmosphere at 50° C. for 2 days. The reaction mixture was diluted with ethyl acetate, and insoluble material was filtered off through celite. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.94 g, 81%).

後処理

  1. filtrationwas filtered off through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9d14606401814237934ab81cd0eae2b2
出典データセット
uspto-grants-2013_08
特許番号
US08501750B2

反応ノート

読み込み中…