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Cesium carbonate → 5-Bromo-1-methyl-3-(pyrazin-2-ylamino)pyridin-2(1H)-one

HRID 407824
ノート
印刷プレビュー

反応式

HRID 407824 の反応式
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].Br[C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([Br:15])[CH:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:15][C:13]1[CH:14]=[C:9]([NH:7][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 78747AminopyrazineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-one

生成物 1

HCID 866840855-Bromo-1-methyl-3-(pyrazin-2-ylamino)pyridin-2(1H)-one収率 47%

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with pyrazin-2-amine (1.0 g, 10 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (2.7 g, 10 mmol), Pd2(dba)3 (460 mg, 0.50 mmol), XantPhos (600 mg, 1.0 mmol), cesium carbonate (6.52 g, 20 mmol), and 1,4-dioxane (150 mL). After three cycles of vacuum/argon flash, the mixture was heated at 100° C. for 2 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by recrystallization with methanol to afford 160a (1.3 g, 47%) as a light green solid. MS-ESI: [M+H]+ 281.0.

後処理

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. filtrationIt was then filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by recrystallization with methanol

出典と根拠

ORDレコード
ord-aeb8b926b46e468baab64cf04dfa9fdd
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754077B2

反応ノート

読み込み中…

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