Triphenylphosphine → 2-Chloro-8-(1-isopropylpiperidin-4-yloxy)quinazoline

HRID 2079631Notes

Reaction equation

HRID 2079631 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.[OH:36][CH:37]1[CH2:42][CH2:41][N:40]([CH:43]([CH3:45])[CH3:44])[CH2:39][CH2:38]1.[Cl:46][C:47]1[N:56]=[CH:55][C:54]2[C:49](=[C:50](O)[CH:51]=[CH:52][CH:53]=2)[N:48]=1>C1COCC1>[Cl:46][C:47]1[N:56]=[CH:55][C:54]2[C:49](=[C:50]([O:36][CH:37]3[CH2:42][CH2:41][N:40]([CH:43]([CH3:45])[CH3:44])[CH2:39][CH2:38]3)[CH:51]=[CH:52][CH:53]=2)[N:48]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 591992302-Chloro-8-quinazolinol

Product 1

HCID 591992192-Chloro-8-(1-isopropylpiperidin-4-yloxy)quinazolineYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0.30M solution of triphenylphosphine (1.5 eq) in THF was added di-tert-butylazodicarboxylate (1.5 eq). The mixture was stirred 15 min at ambient temperature. 4-Hydroxy-1-isopropylpiperidine (4.0 eq) was added. The mixture was stirred 15 min at ambient temperature. 2-Chloroquinazolin-8-ol (1.0 eq) was added. The mixture was stirred an additional 2 h. The crude mixture was concentrated, purified by flash chromatography (EtOAc then 90:10:1 DCM:MeOH:NH4OH), and concentrated to give the desired product in 88% yield. ES/MS m/z 306 (MH+).

Workup

  1. stirringThe mixture was stirred 15 min at ambient temperature
  2. stirringThe mixture was stirred an additional 2 h
  3. concentrationThe crude mixture was concentrated
  4. custompurified by flash chromatography (EtOAc
  5. concentration90:10:1 DCM:MeOH:NH4OH), and concentrated

Sources & evidence

ORD record
ord-6cb201e5246c40fc8dd6d8c4f95e3b75
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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