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4-{4-[2-(2-Hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazin-1-yl}-4-oxo-but-2-enoic acid ethyl ester → 4-Hydroxy-1-{4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazin-1-yl}-4-methyl-pent-2-en-1-one

HRID 2062188
Notes
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Reaction equation

HRID 2062188 reaction equation
C(OC(=O)[CH:5]=[CH:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[N:18]=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[N:16]=2)[CH2:11][CH2:10]1)=[O:8])C.C[Mg]Br>C(OCC)C.O.C(Cl)Cl>[OH:32][C:27]([CH3:28])([CH3:26])[CH:5]=[CH:6][C:7]([N:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[N:18]=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[N:16]=2)[CH2:13][CH2:14]1)=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 1364122494-{4-[2-(2-Hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazin-1-yl}-4-oxo-but-2-enoic acid ethyl esterHCID 178418573HCID 178418573, compound

Product 1

HCID 1364122504-Hydroxy-1-{4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazin-1-yl}-4-methyl-pent-2-en-1-one

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 3283
Diethyl Ether
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 4-{4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazin-1-yl}-4-oxo-but-2-enoic acid ethyl ester (655 mg, 1.47 mmol) in 2 mL of diethyl ether at −20° C. was added methyl magnesium bromide (8.4 mL, 11.7 mmol, 1.4 M THF/Toluene), and the reaction mixture was allowed to warm to 0° C. over 15 minutes The mixture was diluted with 10 mL of water and 15 mL of CH2Cl2. The resulting emulsion was filtered, and the organic layer was separated and dried over Na2SO4. The solvent was removed under reduced pressure to give the alcohol. LC/MS: m/z 433.5 (M+H)+ at 2.56 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationThe resulting emulsion was filtered
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c651314df6bd4f008bc12e6010d1ec56
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08283354B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes