1,2-Diaminocyclohexane → HCID 11996714、化合物

HRID 655861ノート

反応式

HRID 655861 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1(N)CCCCC1N.[NH:21]1[C:25]2=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]2[CH:23]=[N:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu](I)I.C(OCC)(=O)C>[N:11]1[NH:12][C:8]([C:4]2[CH:3]=[C:2]([N:21]3[C:25]4=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]4[CH:23]=[N:22]3)[CH:7]=[CH:6][CH:5]=2)=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 46101,2-DiaminocyclohexaneHCID 62657Potassium Phosphate, TribasicHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 27356133-(3-Bromophenyl)-1H-pyrazole

生成物 1

HCID 11996714HCID 11996714、化合物収率 0.2%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

5-(3-bromo-phenyl)-1H-pyrazole (0.3 g, 1.0 eq, 1.34 mmol) and cyclohexane-1,2-diamine (0.03 g, 0.2 eq, 0.27 mmol) were added to a pre-stirred mixture of 1H-Pyrazolo[3,4-d]pyrimidin-4-ylamine (0.22 g, 1.2 eq, 1.62 mmol), copper iodide (0.013 g, 0.5 eq, 0.68 mmol) and potassium phosphate (0.6 g, 2.1 eq, 2.84 mmol) in DMF (8 ml) under an inert atmosphere. The reaction mixture was then stirred at 110° C. for 24 hours, and allowed to cool to room temperature. Ethyl acetate (8 ml) was then added to the reaction mixture which was then filtered through a plug of silica, which was then washed with a further portion of ethylacetate (20 ml). The filtrate was concentrated to dryness in vacuo and the resultant residue was purified by column chromatography using DCM/MeOH (95:5) as eluent to yield the title compound as an off-white solid (0.9 mg, 0.0003 mmol, 0.2%). LCMS: [M+H]+=277, Rt=1.80 min, 93% purity.

後処理

  1. temperatureto cool to room temperature
  2. filtrationwas then filtered through a plug of silica, which
  3. washwas then washed with a further portion of ethylacetate (20 ml)
  4. concentrationThe filtrate was concentrated to dryness in vacuo
  5. customthe resultant residue was purified by column chromatography

出典と根拠

ORDレコード
ord-185a36f64512478fb6b8733d88e86fcd
出典データセット
uspto-grants-2011_12
特許番号
US08071607B2

反応ノート

読み込み中…