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

HRID 876659Notes

Reaction equation

HRID 876659 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.Cl.[OH:10][CH:11]1[CH2:14][NH:13][CH2:12]1.[OH-].[Na+]>O>[Cl:8][C:6]1[N:7]=[CH:2][N:3]=[C:4]([N:13]2[CH2:14][CH:11]([OH:10])[CH2:12]2)[CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 775312,4-Dichloropyrimidine2×HCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 579250791-(6-Chloropyrimidin-4-yl)azetidin-3-olYield 115.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.2 g (48.7 mmol) 2,4-dichloropyrimidine are initially introduced into 140 ml water. 5.3 g (48.7 mmol) 3-hydroxyazetidine hydrochloride and 48.7 ml 1 N sodium hydroxide solution are added and the mixture is heated at 90° C. for 72 h (the 2,4-dichloropyrimidine being detectably volatile and precipitating in crystalline form on the condenser). The solvent is removed in vacuo and the residue is dried to give 10.4 g of the crude product, which is reacted without further purification.

Workup

  1. customprecipitating in crystalline form on the condenser)
  2. customThe solvent is removed in vacuo
  3. customthe residue is dried

Sources & evidence

ORD record
ord-5b075ba59a9b4b8082cb1b5a68c371b8
Source dataset
uspto-grants-2015_03
Patent number
US08987261B2

Reaction notes

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