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

HRID 1662848노트

반응식

HRID 1662848 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-03f5f319a3304b1a8285dc74cdafe9f3
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030487B2

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