Azetidine → HCID 68058511, compound

HRID 1186806Notes

Reaction equation

HRID 1186806 reaction equation
Cl[C:2]1[C:7]([I:8])=[CH:6][N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:15]1[CH2:18][CH2:17][CH2:16]1>COCCOC>[N:15]1([C:2]2[C:7]([I:8])=[CH:6][N:5]=[CH:4][N:3]=2)[CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 10796Cesium carbonateHCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 68058511HCID 68058511, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 16×100 mm reaction tube under N2 was added 4-chloro-5-iodopyrimidine (200 mg, 0.832 mmol), cesium carbonate (817 mg, 2.508 mmol) and 1,2-dimethoxyethane (5 mL). The reaction mixture was flushed with nitrogen and then treated with azetidine (112 μL, 1.662 mmol). The reaction mixture was securely capped, stirred at room temperature for 5 min, and then heated at 90° C. for 18 h. The reaction mixture was filtered through a small Celite plug by gravity, washed with dichloromethane (70 mL) and the solvent was evaporated off in vacuo to give 200 mg (92%) of the title compound as a pale yellow solid.

Workup

  1. customTo a 16×100 mm reaction tube under N2
  2. customThe reaction mixture was flushed with nitrogen
  3. customThe reaction mixture was securely capped
  4. temperatureheated at 90° C. for 18 h
  5. filtrationThe reaction mixture was filtered through a small Celite plug by gravity
  6. washwashed with dichloromethane (70 mL)
  7. customthe solvent was evaporated off in vacuo

Sources & evidence

ORD record
ord-3763edea823245ffa447335da6bbee6b
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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