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Diisopropylethylamine → N-{5-chloro-2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N,N',N'-trimethylsulfamide

HRID 415403
ノート
印刷プレビュー

反応式

HRID 415403 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:15])[S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[C:5]([Cl:16])=[C:4]([NH:17][C:18]2[CH:22]=[C:21]([CH3:23])[NH:20][N:19]=2)[N:3]=1.Cl.[F:25][C:26]1[CH:27]=[N:28][C:29]([C@@H:32]([NH2:34])[CH3:33])=[N:30][CH:31]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:16][C:5]1[C:6]([N:8]([CH3:15])[S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])=[N:7][C:2]([NH:34][C@H:32]([C:29]2[N:30]=[CH:31][C:26]([F:25])=[CH:27][N:28]=2)[CH3:33])=[N:3][C:4]=1[NH:17][C:18]1[CH:22]=[C:21]([CH3:23])[NH:20][N:19]=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

5

反応物 3

HCID 81531DiisopropylethylamineHCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochlorideHCID 86624839N-{2,5-dichloro-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N,N',N'-trimethylsulfamide

生成物 1

HCID 66624729N-{5-chloro-2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N,N',N'-trimethylsulfamide収率 89.6%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
160 °C

実験手順

A microwave reaction vessel was charged with N-{2,5-dichloro-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N,N′,N′-trimethylsulfamide (Method 24, 83.9 mg, 0.221 mmol), (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 78.4 mg, 0.443 mmol), and DIPEA (0.120 ml, 0.682 mmol). Anhydrous n-BuOH (1 ml) was added, and the tube was sealed and heated in a microwave reactor at 160° C. for 2 hours. The reaction mixture was purified by silica gel chromatography (by ISCO Combiflash with gradient EtOAc and hexane) to afford the title compound as a white solid (95.8 mg, 89.6%). LC-MS, 485 (M+1). 1H-NMR (DMSO-d6, 400 MHz, 80° C.) δ 11.48-12.40 (br, 1H), 8.77 (s, 1H), 7.85-8.66 (br, 1H), 6.98-7.61 (br, 1H), 6.23 (s, 1H), 5.14-5.11 (m, 1H), 2.93 (s, 3H), 2.83 (s, 6H), 2.21 (s, 3H), 1.53 (d, 3H).

後処理

  1. customA microwave reaction vessel
  2. customthe tube was sealed
  3. customThe reaction mixture was purified by silica gel chromatography (by ISCO Combiflash with gradient EtOAc and hexane)

出典と根拠

ORDレコード
ord-1dd3026e4220472288afe2a505166b8f
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08088784B2

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