Triphenylphosphine → HCID 86007768, compound

HRID 640019Notes

Reaction equation

HRID 640019 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]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][CH2:38][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 611632-MorpholinoethanolHCID 97268Di-tert-butyl azodicarboxylateHCID 231324754-Chloro-7-methoxyquinazolin-6-ol

Product 1

HCID 86007768HCID 86007768, compoundYield 76%

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), 2-morpholin-4-ylethanol (0.82 g, 6.26 mmol) and triphenylphosphine (1.8 g, 6.87 mmol) in dichloromethane (25 ml). The reaction mixture was stirred for 2 hour and then the resulting orange solution was purified directly by silica gel chromatography eluting with a mixture of 3% methanol in dichloromethane and then purified further by chromatography on neutral alumina eluting with a 3% mixture of methanol in dichloromethane to give 4-chloro-7-methoxy-6-(2-morpholin-4-ylethoxy)quinazoline (1.40 g, 76% 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 3% methanol in dichloromethane
  3. custompurified further by chromatography on neutral alumina eluting with a 3% mixture of methanol in dichloromethane

Sources & evidence

ORD record
ord-2dfb9c434bfe45ae94f9edc4776731ef
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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