HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Tributylvinyltin → {1-[4-(6-Phenyl-3-vinyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362159
Notes
Print preview

Reaction equation

HRID 2362159 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[C:30](Br)=[CH:31][N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:35]([Sn](CCCC)(CCCC)C=C)[CH2:36]CC>[N+](CC)(CC)(CC)CC.[Cl-].C1COCC1.C(Cl)Cl.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>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[C:30]([CH:35]=[CH2:36])=[CH:31][N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 81998TributylvinyltinHCID 66665726{1-[4-(3-Bromo-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

Product 1

HCID 66719010{1-[4-(6-Phenyl-3-vinyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl EsterYield 86.6%

Reagents, catalysts & solvents 4

HCID 5946Tetraethylammonium ChlorideCatalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6344DichloromethaneSolvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound 4-3 (100 mg 0.193 mmol), Tributyl-vinyl-stannane (92 mg, 0.58 mmol), K2 CO3 (27 mg, 0.193 mmol), Et4NCl (31.8 mg 0.193 mmol) and Pd(PPh3)2Cl2 (10 mg) in THF (5 mL) was heated at 100° C. in microwave system under N2 atmosphere for 45 min. After cooling, the mixture was diluted with 15 mL of DCM, the combined organic phase was washed with 0.1N HClaq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 78 mg of 4-5.

Workup

  1. temperatureAfter cooling
  2. washthe combined organic phase was washed with 0.1N HClaq and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep.TLC

Sources & evidence

ORD record
ord-2dc2e4f172b240d980c21f7670864c00
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691825B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes