Dibutyltin oxide → 5-{1-tert-Butyl-2-[5-(2H-tetrazol-5-yl)-2-[1,2,4]triazol-1-yl-phenyl]-1H-benzoimidazol-5-yl}-pyrimidin-2-ylamine

HRID 1966781ノート

反応式

HRID 1966781 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)[C:18]#[N:19])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.[N:34]([Si](C)(C)C)=[N+:35]=[N-:36].C([Sn](=O)CCCC)CCC>CN(C=O)C>[C:28]([N:12]1[C:11]2[CH:32]=[CH:33][C:8]([C:5]3[CH:6]=[N:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[CH:9][C:10]=2[N:14]=[C:13]1[C:15]1[CH:16]=[C:17]([C:18]2[N:34]=[N:35][NH:36][N:19]=2)[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[N:26][CH:25]=[N:24]1)([CH3:29])([CH3:30])[CH3:31]

参加物

5

反応物 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 532376053-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile

生成物 1

HCID 532382995-{1-tert-Butyl-2-[5-(2H-tetrazol-5-yl)-2-[1,2,4]triazol-1-yl-phenyl]-1H-benzoimidazol-5-yl}-pyrimidin-2-ylamine収率 9.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile (example 7) (100 mg, 0.23 mmol) in DMF (5 mL) are added azidotrimethylsilane (0.06 mL, 0.46 mmol) and dibutyltin oxide (175 mg, 0.69 mmol) at room temperature. The solution is heated up to 100° C. for 5 hours in a microwave reactor. The solution is cooled down and is extracted with Sat. NH4Cl (10 mL) and EtOAc (3×10 mL). The combined organic layer is dried with MgSO4 (500 mg) and is filtered. The filtrate is concentrated and the residue is purified by preparative HPLC to afford the title compound (10 mg, 9%) LCMS (ESMS): m/z: 479.40 (M++1).

後処理

  1. temperatureThe solution is cooled down
  2. extractionis extracted with Sat. NH4Cl (10 mL) and EtOAc (3×10 mL)
  3. dry with materialThe combined organic layer is dried with MgSO4 (500 mg)
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by preparative HPLC

出典と根拠

ORDレコード
ord-ff8f22cc47954896ab5f66f463e7631e
出典データセット
uspto-grants-2013_04
特許番号
US08420655B2

反応ノート

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