Triethylamine → 4-(2,2-Dimethyl-propylamino)-5-{3-[4-(4-methyl-piperazin-1-yl)-phenyl]-prop-1-ynyl}-pyrimidine-2-carbonitrile

HRID 1984236노트

반응식

HRID 1984236 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[CH:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[C:18]1[C:19]([NH:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[N:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1.C(N(CC)CC)C.[Cl-].[NH4+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:29][C:28]([CH3:31])([CH3:30])[CH2:27][NH:26][C:19]1[C:18]([C:16]#[C:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)=[CH:23][N:22]=[C:21]([C:24]#[N:25])[N:20]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrileHCID 577141261-Methyl4-(4-prop-2-ynyl-phenyl)-piperazine

생성물 1

HCID 444502714-(2,2-Dimethyl-propylamino)-5-{3-[4-(4-methyl-piperazin-1-yl)-phenyl]-prop-1-ynyl}-pyrimidine-2-carbonitrile수율 25%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 1-methyl-4-(4-prop-2-ynyl-phenyl)-piperazine (0.75 mmol) and 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (0.5 mmol) in THF (7 ml), triethylamine (1.5 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.025 mmol) and copper (I) iodide (0.05 mmol) are added. The reaction mixture is heated at 60° C. ca. for 3 h. Saturated aqueous solution of ammonium chloride is added to the reaction mixture and then aqueous layer is extracted with two 50 ml portions of AcOEt. The combined extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum to give crude product which is purified by reverse phase HPLC. Yield: 25%. Rf=0.5 (MeOH:CH2Cl2=5:95)

후처리

  1. extractionaqueous layer is extracted with two 50 ml portions of AcOEt
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give crude product which
  6. customis purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-6f7e1074d73f41fa895178e9b5ac46a8
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544688B2

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