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Cesium carbonate → tert-butyl 9-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1478047
ノート
印刷プレビュー

反応式

HRID 1478047 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:11][CH2:10]2)[C:5]([Cl:27])=[CH:4][N:3]=1.[CH3:28][N:29]1[CH:33]=[C:32]([NH2:34])[N:31]=[CH:30]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:27][C:5]1[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][C:12]3([CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[CH2:18][CH2:19]3)[CH2:13][CH2:14]2)=[N:7][C:2]([NH:34][C:32]2[N:31]=[CH:30][N:29]([CH3:28])[CH:33]=2)=[N:3][CH:4]=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 634876Binap, (A+-)-HCID 108986491-Methyl-1H-imidazol-4-amineHCID 118390013Tert-butyl 3-[(2,5-dichloropyrimidin-4-yl)amino]-9-azaspiro[5.5]undecane-9-carboxylate

生成物 1

HCID 118389996tert-butyl 9-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate
収率 50.97%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

To a solution of tert-butyl 3-[(2,5-dichloropyrimidin-4-yl)amino]-9-azaspiro[5.5]undecane-9-carboxylate (500 mg, 1.204 mmol), 1-methylimidazol-4-amine (176.1 mg, 1.813 mmol) and cesium carbonate (1.19 g, 3.65 mmol) in anhydrous dioxane (10 mL) were added BINAP (148.6 mg, 0.2386 mmol) and Pd(OAc)2 (54.1 mg, 0.241 mmol). The reaction was under an inert atmosphere and stirred at 150° C. under microwave irradiation for 2 h. The reaction solution was concentrated in vacuo and the residue was purified by silica gel column chromatography with (DCM/MeOH (v/v)=30/1) to give the title compound as a yellow solid (292 mg, 50.97%).

後処理

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography with (DCM/MeOH (v/v)=30/1)

出典と根拠

ORDレコード
ord-a1f87d6ca56a440e8e8b317dc0133db0
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09403801B2

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