Hexane → Tert-butyl 4-(5-ethylpyrimidin-2-yl)piperazine-1-carboxylate

HRID 271558

反応式

HRID 271558 の反応式
[N:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:11]1[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1.CCC[CH2:22][CH2:23][CH3:24].[CH3:25]COC(C)=O>CCO.C(N(CC)CC)C>[C:23]([O:8][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:11]2[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=2)[CH2:3][CH2:2]1)=[O:9])([CH3:22])([CH3:24])[CH3:25]

参加物

7

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 131766Piperazine-1-carboxylic acidHCID 35727632-Chloro-5-ethylpyrimidine

生成物 1

HCID 53305712Tert-butyl 4-(5-ethylpyrimidin-2-yl)piperazine-1-carboxylate収率 41%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8471Triethylamine溶媒

実験手順

To piperazine-1-carboxylic acid .tert.-butyl ester (3.543 mmol) in EtOH (13 ml), triethylamine (1.5 ml) and 2-chloro-5-ethyl-pyrimidine (3.540 mmol) are added. The mixture is refluxed with stirring for 6 h. After cooling at room temperature, the reaction mixture is quenched with an ice water and extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and concentrated to give the product in 41% yield. Rf=0.45 (n-hexane:AcOEt=10:1) 1H NMR(400 MHz, CDCl3) δ 1.19 (t, 3H), 1.49 (s, 9H), 2.47 (q, 2H), 3.49 (dd, 4H), 3.76 (dd, 4H), 8.18 (s, 2H)

後処理

  1. temperatureThe mixture is refluxed
  2. customthe reaction mixture is quenched with an ice water
  3. extractionextracted with AcOEt
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give the product in 41% yield

出典と根拠

ORDレコード
ord-89bb9428f6594941ac30e5acc50f4b5d
出典データセット
uspto-grants-2008_11
特許番号
US07452886B2

関連ノート

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