Sodium Hydroxide → 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol

HRID 1969637Notes

Reaction equation

HRID 1969637 reaction equation
[OH-].[Na+].C([O:11][CH:12]1[CH2:16][CH:15]([C:17]2[N:21]3[C:22]4[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:23]=4[N:24]=[CH:25][C:20]3=[N:19][N:18]=2)[CH:14]([CH2:37][CH3:38])[CH2:13]1)(=O)C1C=CC=CC=1>CO>[CH2:37]([CH:14]1[CH:15]([C:17]2[N:21]3[C:22]4[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[C:23]=4[N:24]=[CH:25][C:20]3=[N:19][N:18]=2)[CH2:16][CH:12]([OH:11])[CH2:13]1)[CH3:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 585578993-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate

Product 1

HCID 585572033-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanolYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of NaOH (0.088 g, 2.20 mmol) in MeOH (8 mL) was added a solution of 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate (0.158 g, 0.312 mmol, prepared using KK from Preparation #20.2) in MeOH (2 mL). The reaction mixture was stirred at ambient temperature for about 3 h. The solvent was removed under reduced pressure and DCM (150 mL) was added. The organic layer was washed with water (5 mL), saturated aqueous NaHCO3 (15 mL), brine (15 mL), and dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol (0.123 g, 98%) as clear oil: LC/MS (Table 1, Method b) Rt=2.34 min; MS m/z: 402 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure and DCM (150 mL)
  2. additionwas added
  3. washThe organic layer was washed with water (5 mL), saturated aqueous NaHCO3 (15 mL), brine (15 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-781dcf4db98f482c8355d9668d1dac0d
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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