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Diisopropylethylamine → N-{2-chloro-5-fluoro-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamide

HRID 415433
ノート
印刷プレビュー

反応式

HRID 415433 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([F:14])=[C:4](Cl)[N:3]=1.[CH3:16][C:17]1[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([F:14])=[C:4]([NH:22][C:19]2[CH:18]=[C:17]([CH3:16])[NH:21][N:20]=2)[N:3]=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 931461H-Pyrazol-3-amine, 5-methyl-HCID 86624844N-(2,6-dichloro-5-fluoro-pyrimidin-4-yl)-N-methyl-methanesulfonamide

生成物 1

HCID 86624842N-{2-chloro-5-fluoro-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamide収率 95%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of N-(2,6-dichloro-5-fluoropyrimidin-4-yl)-N-methylmethanesulfonamide (Method 31, 914 mg, 3.35 mmol) in n-BuOH (3 ml) was added 5-methyl-1H-pyrazol-3-amine (351 mg, 3.62 mmol, 97% purity) and DIPEA (1.2 ml, 6.9 mmol). The mixture was heated at 50° C. overnight. LC/MS showed the completion of the reaction. The solvent was evaporated and the residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-5% methanol in DCM with 1% NH4OH) to afford the title compound as a light yellow solid (1.06 g, 95%). LC-MS, 335 (M+1). NMR (DMSO-d6, 400 MHz) δ12.27 (s, 1H), 10.53 (s, 1H), 6.32 (s, 1H), 3.27 (s, 3H), 3.20 (s, 3H), 2.25 (s, 3H).

後処理

  1. customthe completion of the reaction
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-5% methanol in DCM with 1% NH4OH)

出典と根拠

ORDレコード
ord-f4dec7189bb04bbf88f0d922c070011a
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…

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