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

HRID 1804641
Notes
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Reaction equation

HRID 1804641 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2a8a8727f1154d5cbd4afb00ff1aaf46
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354403B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes