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

HRID 1804641
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HRID 1804641 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2a8a8727f1154d5cbd4afb00ff1aaf46
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08354403B2

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