Morpholine → 4-(5-Iodopyrimidin-4-yl)morpholine

HRID 871129Notes

Reaction equation

HRID 871129 reaction equation
Cl[C:2]1[C:7]([I:8])=[CH:6][N:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[I:8][C:7]1[C:2]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:3][CH:4]=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 654184374-(5-Iodopyrimidin-4-yl)morpholineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a vial containing a solution of 4-chloro-5-iodopyrimidine (0.200 g, 0.832 mmol) in DMF (1.333 mL) was added morpholine (0.291 mL, 3.33 mmol) followed by cesium carbonate (0.542 g, 1.664 mmol). The vial was sealed with a Teflon cap and heated at 90° C. for 80 min, then allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with CH2Cl2. The filtrate was concentrated, then further dried under high vacuum to afford the title compound (235 mg, 97%). ESI MS (M+H)+=292.0.

Workup

  1. customcap
  2. temperatureto cool to room temperature
  3. filtrationThe reaction mixture was filtered through a disposable fritted funnel
  4. washthe filter cake washed with CH2Cl2
  5. concentrationThe filtrate was concentrated
  6. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-bdc1b6ac7ccd4d4a9245dd130625dff6
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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