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Sodium Iodide → Tert-butyl 4-(1-quinazolin-2-ylethyl)piperazine-1-carboxylate

HRID 1804641
ノート
印刷プレビュー

反応式

HRID 1804641 の反応式
Br[CH2:2][C:3]1[N:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[C:26]([O-])([O-])=O.[K+].[K+].[I-].[Na+]>C(#N)C>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[N:12][C:3]=1[CH:2]([N:23]1[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:25][CH2:24]1)[CH3:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 218511882-(1-Bromomethyl)quinazoline

生成物 1

HCID 67986532Tert-butyl 4-(1-quinazolin-2-ylethyl)piperazine-1-carboxylate収率 42%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

To a mixture of the title compound from Step C (240 mg, 1.01 mmol) and N—BOC-piperazine (189 mg, 1.01 mmol), in acetonitrile (5 ml) was added K2CO3 (210 mg, 1.52 mmol) and sodium iodide (152 mg, 1.01 mmol) and the resulting mixture heated at reflux overnight. The mixture cooled and partitioned between water and EtOAc; organic layer washed with sat. NaCl, dried over MgSO4, filtered and evaporated. The residue purified by column chromatography (eluent: 5% MeOH in DCM) to afford the title compound 145 mg (42%) as an orange oil, which solidified on standing. 1H NMR (CDCl3): 1.45 (s, 9H), 1.60 (d, J 6.8 Hz, 3H), 2.46 (m, 2H), 2.69 (m, 2H), 3.49 (m, 4H), 3.97 (q, J 6.8 Hz, 1H), 7.66 (m, 1H), 7.93 (m, 2H), 8.06 (d, J 8.3 Hz, 1H), 9.44 (s, 1H).

後処理

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture cooled
  4. custompartitioned between water and EtOAc
  5. washorganic layer washed with sat. NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue purified by column chromatography (eluent: 5% MeOH in DCM)

出典と根拠

ORDレコード
ord-2a8a8727f1154d5cbd4afb00ff1aaf46
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354403B2

反応ノート

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