Ethanol → HCID 86725297, compound

HRID 1403229Notes

Reaction equation

HRID 1403229 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([O:31]CC)=[O:30])[CH:9]=2)[C:5]([C:34]#[C:35][Si](C)(C)C)=[CH:4][N:3]=1.[OH-].[K+].CCO>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([OH:31])=[O:30])[CH:9]=2)[C:5]([C:34]#[CH:35])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 86725296HCID 86725296, compound

Product 1

HCID 86725297HCID 86725297, compoundYield 95%

Conditions

Temperature
50 °C

Procedure

Ethyl 5-{2-amino-5-[(trimethylsilyl)ethynyl]pyrimidin-4-yl}-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylate (466 mg, 0.8 mmol) was treated with a 1.5 M solution of potassium hydroxide in 95% EtOH (5.33 mL, 8 mmol) and stirred at 50° C. overnight. After cooling, the residue was concentrated, dissolved in water and washed with DCM. The aqueous layer was acidified until pH<1 with the addition of 2 N HCl and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and the solvent evaporated under vacuum to obtain the title compound as an orange oil (367 mg, 95%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe residue was concentrated
  3. dissolutiondissolved in water
  4. washwashed with DCM
  5. additionThe aqueous layer was acidified until pH<1 with the addition of 2 N HCl
  6. extractionextracted with EtOAc (3×)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-ebf6fc6c55364864927e020fdc38f018
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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