Ethanol → 8-Isopropoxy-2-methyl-4-phenyl-quinazoline

HRID 640786Notes

Reaction equation

HRID 640786 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH:13]([CH3:15])[CH3:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:16])[N:3]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC=CC=1>[CH:13]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:16])[N:3]=[C:2]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 592566944-Chloro-8-isopropoxy-2-methyl-quinazoline

Product 1

HCID 592566498-Isopropoxy-2-methyl-4-phenyl-quinazoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Procedure

To a stirred mixture of 4-chloro-8-isopropoxy-2-methyl-quinazoline (35) (0.58 mmol), phenylboronic acid (0.62 mmol), 2 N Na2CO3 (7.2 mL), EtOH (1.2 mL) and benzene (6 mL) was added, under a blanket of argon, Pd(PPh3)4 (20 mg). The mixture was stirred under reflux for 16 h, cooled, and concentrated. Subsequent column chromatography (ethyl acetate/hexane) provided 8-isopropoxy-2-methyl-4-phenyl-quinazoline (36) as a solid.

Workup

  1. temperatureunder reflux for 16 h
  2. temperaturecooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-98787b82a8bb43a79cf632c7b07856d8
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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