Sodium hydride → HCID 71648594, compound

HRID 645495Notes

Reaction equation

HRID 645495 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[C:22]([S:27][CH3:28])[N:21]=1>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][O:18][C:24]2[CH:25]=[C:20]([Cl:19])[N:21]=[C:22]([S:27][CH3:28])[N:23]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 71648594HCID 71648594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (6.4 mmol) is added to a solution of 4-(2-hydroxy-ethyl)piperidine-1-carboxylic acid tert-butyl ester (5.3 mmol) in THF (10 mL) at 0° C. After stirring at room temperature for 30 min, a solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine (5.3 mmol) in THF (10 mL) is added dropwise to the reaction mixture. The reaction mixture is stirred at room temperature for 12 h and quenched by H2O. The mixture is extracted with AcOEt. The organic layer is washed with H2O, dried over MgSO4 and evaporated in vacuo to give a crude 4-[2-(6-chloro-2-methylsulfanylpyrimidin-4-yloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 12 h
  2. customquenched by H2O
  3. extractionThe mixture is extracted with AcOEt
  4. washThe organic layer is washed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-75b1a57c11ca41dbb86517c1afd7a7de
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

Loading…