Triphenylphosphine → 4-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazoline

HRID 640017

Reaction equation

HRID 640017 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[Cl:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:29][CH3:30])=[C:25]([OH:28])[CH:26]=2)[N:21]=[CH:20][N:19]=1.[N:31]1([CH2:37][CH2:38][CH2:39]O)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Cl:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:29][CH3:30])=[C:25]([O:28][CH2:39][CH2:38][CH2:37][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:26]=2)[N:21]=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 1995763-Morpholino-1-propanolHCID 231324754-Chloro-7-methoxyquinazolin-6-ol

Product 1

HCID 226492214-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazolineYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl azodicarboxylate (1.44 g, 6.26 mmol) was added portionwise at room temperature to a stirred suspension of 4-chloro-7-methoxyquinazolin-6-ol (1.20 g, 5.70 mmol), 3-morpholin-4-ylpropan-1-ol (0.91 g, 6.27 mmol) and triphenylphosphine (1.8 g, 6.87 mmol) in dichloromethane (25 ml). The reaction mixture was stirred for 2 hours and then the resulting orange solution was purified directly by silica gel chromatography eluting with a mixture of 5% methanol in dichloromethane to give 4-chloro-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazoline (1.28 g, 67% yield) as a pale yellow solid:

Workup

  1. customthe resulting orange solution was purified directly by silica gel chromatography
  2. washeluting with a mixture of 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-179dc28d5c1e40fca6dc9873b75a4041
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Linked notes

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