Cesium carbonate → (5-Nitro-pyrimidin-2-yl)-(4-(3-pyrrolidin-1-yl-propyl)-phenyl)-amine

HRID 1662848ノート

反応式

HRID 1662848 の反応式
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].Br[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:14][CH:13]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[N:6][C:7]([NH:10][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:16][CH:17]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 764905-Nitropyrimidin-2-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 248235691-(3-(4-Bromophenyl)propyl)pyrrolidine

生成物 1

HCID 58748709(5-Nitro-pyrimidin-2-yl)-(4-(3-pyrrolidin-1-yl-propyl)-phenyl)-amine収率 56%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-nitro-pyrimidin-2-ylamine (0.15 g, 1.1 mmol), intermediate 51 (Example 101) (0.30 g, 1.1 mmol), Pd2(dba)2 (75 mg, 0.082 mmol), Xantphos (96 mg, 0.17 mmol) and cesium carbonate (0.69 g, 2.1 mmol) was suspended in dioxane (15 mL) and heated at reflux under the argon atmosphere for 15 h. The mixture was allowed to cool to room temperature, filtered and washed with DCM. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (10% MeOH/DCM to 20% MeOH and 2% TEA/DCM) to afford the title compound as a yellow solid (0.20 g, 56%).

後処理

  1. temperatureheated
  2. temperatureat reflux under the argon atmosphere for 15 h
  3. filtrationfiltered
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by flash chromatography on silica gel (10% MeOH/DCM to 20% MeOH and 2% TEA/DCM)

出典と根拠

ORDレコード
ord-03f5f319a3304b1a8285dc74cdafe9f3
出典データセット
uspto-grants-2011_10
特許番号
US08030487B2

反応ノート

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