Sodium Hydroxide → 1-(6-Chloropyrimidin-4-yl)azetidin-3-ol

HRID 2039476Notes

Reaction equation

HRID 2039476 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[OH-].[Na+].[OH:11][CH:12]1[CH2:15][NH:14][CH2:13]1>O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:14]2[CH2:15][CH:12]([OH:11])[CH2:13]2)[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 709434,6-DichloropyrimidineHCID 15142903-Hydroxyazetidine

Product 1

HCID 579250791-(6-Chloropyrimidin-4-yl)azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

7.3 g (48.7 mmol) of 4,6-dichloropyrimidine are suspended in 140 ml of water, and 47 ml 1 N aqueous sodium hydroxide solution are added. 5.3 g (48.7 mmol) of 3-hydroxyazetidine are added, and the reaction mixture is stirred at 90° C. for 3 d. After cooling to RT, the reaction mixture is concentrated under reduced pressure and reacted further without further purification.

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customreacted further without further purification

Sources & evidence

ORD record
ord-d677e3e30a6c49f8993e48c219d89591
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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