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Sodium Carbonate → tert-butyl-N-methyl-N-[1-oxo-1-[[5-pyrimidin-5-yl-6-[2-tri(propan-2-yl)silyl-ethynyl]pyridin-2-yl]amino]propan-2-yl]carbamate

HRID 535400
ノート
印刷プレビュー

反応式

HRID 535400 の反応式
[C:1]([O:5][C:6](=[O:33])[N:7]([CH:9]([CH3:32])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([C:20]#[C:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[N:34]1[CH:39]=[C:38](B(O)O)[CH:37]=[N:36][CH:35]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>[C:1]([O:5][C:6](=[O:33])[N:7]([CH3:8])[CH:9]([CH3:32])[C:10](=[O:11])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:38]2[CH:39]=[N:34][CH:35]=[N:36][CH:37]=2)=[C:15]([C:20]#[C:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[N:14]=1)([CH3:4])([CH3:3])[CH3:2]
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

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86694383Tert-butyl (1-((5-bromo-6-((triisopropylsilyl)ethynyl)pyridin-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

生成物 1

HCID 86694384tert-butyl-N-methyl-N-[1-oxo-1-[[5-pyrimidin-5-yl-6-[2-tri(propan-2-yl)silyl-ethynyl]pyridin-2-yl]amino]propan-2-yl]carbamate

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

A mixture of tert-butyl-N-[1-[[5-bromo-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-yl]-amino]-1-oxopropan-2-yl]-N-methylcarbamate C1a (3.5 g, 6.5 mmol), pyrimidin-5-ylboronic acid (1.0 g, 7.8 mmol), Na2CO3 (1.4 g, 13.2 mmol), Dichlorobis(triphenylphosphine)palladium(II) (450 mg, 0.64 mmol), dioxane (20 ml), MeOH (5 ml) and water (3.5 ml) is stirred under argon atmosphere for 17 h at 80° C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 2.33 g (67%). HPLC-MS: M+H=538; tR=2.26 min (*Method—4).

後処理

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

出典と根拠

ORDレコード
ord-4f63e138e343479a96c422c11a5bd43b
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859541B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート