Sodium Hydroxide → (R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(4-(methylsulfonyl)phenyl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

HRID 44847ノート

反応式

HRID 44847 の反応式
Br[C:2]1[N:3]([C:7]2[N:16]=[CH:15][C:14]3[N:13]([CH3:17])[C:12](=[O:18])[C@@H:11]([CH2:19][CH3:20])[N:10]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[C:9]=3[N:8]=2)[CH:4]=[CH:5][N:6]=1.[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28].[OH-].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:21]1([N:10]2[C:9]3[N:8]=[C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[C:33]4[CH:34]=[CH:35][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:31][CH:32]=4)[N:16]=[CH:15][C:14]=3[N:13]([CH3:17])[C:12](=[O:18])[C@H:11]2[CH2:19][CH3:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 58405307(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

生成物 1

HCID 58405285(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(4-(methylsulfonyl)phenyl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one収率 2.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65, 0.15 g, 0.37 mmol), 4-(methylsulfonyl)phenylboronic acid (0.148 g, 0.74 mmol), aqueous sodium hydroxide (240 μL of 3N) and Pd(PPh3)4 (42 mg, 0.037 mmol) were dissolved in 1.2 mL of DME/H2O (5/1, v/v) and a stream of nitrogen was bubbled through the mixture for 2 minutes. The resulting solution was stirred at 90° C. for 18 h. The reaction mixture was diluted with brine, extracted with EtOAc, dried with Na2SO4 then purified by silica gel column chromatography and preparative HPLC to give to give the title compound (3.8 mg). LCMS: 481.2 m/z (M+H)+; ret. Time: 6.19 min (Analytical Method C).

後処理

  1. customv/v) and a stream of nitrogen was bubbled through the mixture for 2 minutes
  2. additionThe reaction mixture was diluted with brine
  3. extractionextracted with EtOAc
  4. dry with materialdried with Na2SO4
  5. customthen purified by silica gel column chromatography and preparative HPLC
  6. customto give

出典と根拠

ORDレコード
ord-918dc09751b445d69dbea96e140006a7
出典データセット
uspto-grants-2013_09
特許番号
US08541418B2

反応ノート

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