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Pentamethyldiethylenetriamine → (4-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

HRID 2105065
Notes
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Reaction equation

HRID 2105065 reaction equation
[Li]CCCC.[C:6]([Si:10]([O:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH3:22])([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].CN(CCN(CCN(C)C)C)C.[CH3:35][N:36]1[C:40]([CH:41]=[O:42])=[N:39][C:38]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N:37]1>C1COCC1.O>[Si:10]([O:13][C:14]1[C:15]([CH2:21][CH3:22])=[CH:16][C:17]([CH:41]([C:40]2[N:36]([CH3:35])[N:37]=[C:38]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:39]=2)[OH:42])=[C:18]([F:20])[CH:19]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 18196PentamethyldiethylenetriamineHCID 132241431-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehydeHCID 57803899Tert-butyl(2-ethyl-5-fluorophenoxy)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 57803708(4-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanolYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

BuLi (0.67 mL, 1.6 M in hexanes, 1.1 mmol) was added dropwise to a solution of Intermediate 386.3 (250 mg, 0.98 mmol) and PMDTA (0.20 mL, 0.98 mmol) in THF (4 mL) at −78° C. The mixture was warmed to −40° C. and stirred for 30 min. After recooling the reaction to −78° C., Intermediate 386.1 (203 mg, 1.08 mmol) in THF (2 mL) was added and the mixture was warmed to ambient temperature over 2 h. Water was added to the mixture and it was extracted with EtOAc. The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (hexanes, EtOAc) yielded 292 mg of Intermediate 386.4 as a clear oil. LCMS 442.34 (M+H).

Workup

  1. customthe reaction to −78° C.
  2. temperaturethe mixture was warmed to ambient temperature over 2 h
  3. extractionwas extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography (hexanes, EtOAc)

Sources & evidence

ORD record
ord-5e6655e0ae8245958850c9e5e6945c7e
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576098B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes