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

HRID 1163008
ノート
印刷プレビュー

反応式

HRID 1163008 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒

実験手順

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),

後処理

  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

出典と根拠

ORDレコード
ord-9e4594239c634b6891bbafd8b16eadac
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820818B2

反応ノート

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