Diisopropylethylamine → 1-[4-(6-Chloro-pyrimidin-4-ylmethyl)-phenyl]-3-(4-ethyl-phenyl)-urea

HRID 1993552ノート

反応式

HRID 1993552 の反応式
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH:12]=1.[CH2:25]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1)[CH3:26]>C1COCC1>[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:34]([NH:33][C:30]3[CH:31]=[CH:32][C:27]([CH2:25][CH3:26])=[CH:28][CH:29]=3)=[O:35])=[CH:20][CH:19]=2)[CH:12]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 900074-Ethylphenyl isocyanateHCID 858915834-(6-Chloro-pyrimidin-4-ylmethyl)-phenylamine

生成物 1

HCID 586593551-[4-(6-Chloro-pyrimidin-4-ylmethyl)-phenyl]-3-(4-ethyl-phenyl)-urea

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A 4 N solution of HCl in dioxane (1.2 mL, 4.96 mmol, 30 equiv) is added to a solution of [4-(6-chloro-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (50 mg, 0.156 mmol) in CH2Cl2 (0.67 mL), under an argon atmosphere. The resulting white suspension is stirred at rt for 4 h and concentrated in vacuo to afford 50.9 mg of crude 4-(6-chloro-pyrimidin-4-ylmethyl)-phenylamine as a white solid. DIEA (80 μL, 0.454 mmol, 2 equiv) is added to a suspension of crude 4-(6-chloro-pyrimidin-4-ylmethyl)-phenylamine (50 mg, 0.227 mmol) in THF (0.4 mL), under an argon atmosphere. 4-Ethyl-phenyl-isocyanate (40 μL, 0.250 mmol, 1.1 equiv) is then added. The resulting yellow solution is stirred at rt for 2 h and concentrated in vacuo. The residue is purified by silica gel (20 g) column chromatography (CH2Cl2/MeOH, 98/2). A second purification affords the title compound as a white solid: ES-MS: 367.0 [M+H]+; single peak at tR=8.94 min (System 2); Rf=0.32 (CH2Cl2/MeOH, 95/5).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by silica gel (20 g) column chromatography (CH2Cl2/MeOH, 98/2)
  3. customA second purification

出典と根拠

ORDレコード
ord-4059465bb73e4761a853cb2e376fa36e
出典データセット
uspto-grants-2010_01
特許番号
US07652022B2

反応ノート

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