1,1'-Carbonyldiimidazole → 1-(4-(2-Aminopyrimidin-4-yloxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1 H-pyrazol-5-yl)urea

HRID 2069152ノート

反応式

HRID 2069152 の反応式
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[C:13]([C:17]1[CH:21]=[C:20]([NH2:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:18]=1)([CH3:16])([CH3:15])[CH3:14].[NH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([O:41][C:42]2[CH:47]=[CH:46][N:45]=[C:44]([NH2:48])[N:43]=2)=[CH:33][CH:32]=1>C(Cl)Cl>[NH2:48][C:44]1[N:43]=[C:42]([O:41][C:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:31]([NH:30][C:6]([NH:22][C:20]3[N:19]([C:23]4[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=4)[N:18]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:21]=3)=[O:7])=[CH:32][CH:33]=2)[CH:47]=[CH:46][N:45]=1

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineHCID 207688484-(4-Aminonaphthalen-1-yloxy)pyrimidin-2-amine

生成物 1

HCID 585647671-(4-(2-Aminopyrimidin-4-yloxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1 H-pyrazol-5-yl)urea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a suspension of CDI (17.24 g, 106 mmol) in DCM (150 mL) was added 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (24.38 g, 106 mmol) in 1 g portions over 40 min and the reaction stirred at RT for 2 hr. An aliquot of this solution (5.0 mL,) was added dropwise to a suspension of 4-(4-aminonaphthalen-1-yloxy)pyrimidin-2-amine (720 mg, 2.85 mmol) in DCM (15 mL) and the mixture maintained at RT for 2 hr. The reaction mixture was diluted with DCM (20 mL) and was washed with water (30 mL) and brine (30 mL) and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 20-60%, gradient elution) to afford the title compound, Intermediate P1, as a beige solid (1.21 g, 83%); Rt 2.12 min (Method 2); m/z 508 (M+H)+, (ES+)+.

後処理

  1. temperaturethe mixture maintained at RT for 2 hr
  2. washwas washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 20-60%, gradient elution)

出典と根拠

ORDレコード
ord-028e52a3706244c89489050c2b0fd5fc
出典データセット
uspto-grants-2012_10
特許番号
US08299074B2

反応ノート

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