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Triethylamine → 4-Cyclopentylamino-5-(4-phenyl-but-1-ynyl)-pyrimidine-2-carbonitrile

HRID 1163008
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HRID 1163008 반응식
Br[C:2]1[C:3]([NH:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:16]1([CH2:22][CH2:23][C:24]#[CH:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.[Cl-].[NH4+]>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>[CH:11]1([NH:10][C:3]2[C:2]([C:25]#[C:24][CH2:23][CH2:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:7][N:6]=[C:5]([C:8]#[N:9])[N:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 1233604-Phenyl-1-butyneHCID 686474045-Bromo-4-cyclopentylamino-pyrimidine-2-carbonitrile

생성물 1

HCID 102452344-Cyclopentylamino-5-(4-phenyl-but-1-ynyl)-pyrimidine-2-carbonitrile수율 89.9%

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매

실험 절차

5-Bromo-4-cyclopentylamino-pyrimidine-2-carbonitrile (0.69 mmol), 4-phenyl-1-butyne (1.66 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.035 mmol), copper (I) iodide (0.07 mmol) and triethylamine (2.1 mmol) in D (5 ml) is stirred at 75° C. for 2.5 h. The reaction mixture is treated with saturated ammonium chloride and extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. The crude product is applied to a silica gel column chromatography, which is eluted with following solvents: n-hexane:AcOEt=12:1 (v/v) and n-hexane:AcOEt=10:1 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 89.9%, Rf=0.65 (n-hexane:AcOEt=2:1). 1H-NMR (400 MHz, CDCl3) δ 1.26-1.33 (m, 2H), 1.64-1.71 (m, 4H), 2.05-2.09 (m, 3H), 2.79-2.86 (m, 2H), 2.94-3.00 (m, 2H), 4.30-4.38 (m, 2H), 5.36-5.34 (m, 1H), 7.35-7.21 (m, 5H), 8.10 (s, 1H),

후처리

  1. extractionextracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down
  5. washis eluted with following solvents
  6. customThe solvent of the latter effluent is removed by evaporation
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-9e4594239c634b6891bbafd8b16eadac
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07820818B2

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