Sodium Iodide → 5-Bromo-1-(2-morpholinoethyl)pyrimidin-2(1H)-one

HRID 418739Notes

Reaction equation

HRID 418739 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178517598HCID 178517598, compound

Product 1

HCID 587904085-Bromo-1-(2-morpholinoethyl)pyrimidin-2(1H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-2-hydroxypyrimidine (1.00 g, 5.75 mmol) in DMF (19 mL) was added sodium iodide (1.29 g, 8.6 mmol), cesium carbonate (4.68 g, 14.4 mmol), 4-(2-chloroethyl)morpholine hydrochloride (1.18 g, 6.32 mmol) and the reaction mixture was stirred at 60° C. for 2.5 h. The solution was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography, eluting with gradient of methanol (5-15%) in dichloromethane to give title compound 413 (1.29 g, 78% yield). MS (m/z): 288.1 (50%) (M+H), 290.0 (50%) (M+H). 1H NMR (DMSO-d6) δ (ppm): 8.61 (d, J=3.3 Hz, 1H), 8.46 (d, J=3.3 Hz, 1H), 3.93 (t, J=5.9 Hz, 2H), 3.51 (t, J=4.5 Hz, 4H), 2.57 (t, J=6.1 Hz, 2H), 2.45-2.39 (m, 4H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with gradient of methanol (5-15%) in dichloromethane

Sources & evidence

ORD record
ord-1fd6d4c52cbc4aa985faedac9e3f9a18
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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