Cesium carbonate → [4-(2-Hydroxy-ethyl)-piperazin-1-yl]-[5-(5-nitro-pyrimidin-2-ylamino)-Pyridin-2-yl]methanone

HRID 1662844

반응식

HRID 1662844 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:13]=[CH:14][C:15]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][OH:28])[CH2:22][CH2:21]2)=[O:19])=[N:16][CH:17]=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.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:28][CH2:27][CH2:26][N:23]1[CH2:22][CH2:21][N:20]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([NH:10][C:7]3[N:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=3)=[CH:17][N:16]=2)=[O:19])[CH2:25][CH2:24]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 764905-Nitropyrimidin-2-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58748747(5-Bromo-pyridin-2-yl)-(4-(2-hydroxy-ethyl)-piperazin-1-yl)-methanone

생성물 1

HCID 58748708[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-[5-(5-nitro-pyrimidin-2-ylamino)-Pyridin-2-yl]methanone수율 40%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5-nitro-pyrimidin-2-ylamine (0.85 g, 6.1 mmol), intermediate 46 (Example 95) (2.5 g, 8.0 mmol), Pd(OAc)2 (0.40 g, 0.44 mmol), Xantphos (0.5 g, 0.86 mmol) and cesium carbonate (4.0 g, 12 mmol) was suspended in dioxane (30 mL) and heated at reflux under the argon atmosphere for 18 h. The mixture was allowed to cool to room temperature, filtered and washed with DCM. The filtrate was concentrated and the crude product purified by flash chromatography on silica gel (5% MeOH/DCM to 15% MeOH/DCM) to afford the title compound (0.90 g, 40%) as a yellow solid.

후처리

  1. temperatureheated
  2. temperatureat reflux under the argon atmosphere for 18 h
  3. filtrationfiltered
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated
  6. customthe crude product purified by flash chromatography on silica gel (5% MeOH/DCM to 15% MeOH/DCM)

출처 및 근거

ORD 기록
ord-34d0626db6e243d694b35cb2bc284c9b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030487B2

연결된 노트

불러오는 중…