Morpholine → HCID 59198411, compound

HRID 1920815Notes

Reaction equation

HRID 1920815 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:10]=2)[N:3]=1.CCN(C(C)C)C(C)C.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 59198382HCID 59198382, compound

Product 1

HCID 59198411HCID 59198411, compoundYield 38,540%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2,4-dichloro-6-(3-(methylsulfonyl)phenyl)pyrimidine (220 mg, 0.72 mmol, 1 eq) was dissolved in EtOH (5 mL) and DIEA was added (0.31 mL, 2.2 mmol, 3 eq). The reaction mixture was cooled to 0° C. and morpholine (94 mg, 1.1 μmol, 1.6 eq) was added. The reaction mixture was stirred at room temperature for 3 days. The ethanol was concentrated under reduced pressure and the residue was partitioned between EtOAc and sat. aq. NaHCO3. The organic layer was separated, washed with water and dried (Na2SO4). The residue was purified by column chromatography on silica gel (3% EtOAc/DCM to 40% EtOAc/DCM) to obtained the desired product (150 mg, 58%). LCMS (m/z): 302.8 (MH+), Rt: 1.51 min.

Workup

  1. concentrationThe ethanol was concentrated under reduced pressure
  2. customthe residue was partitioned between EtOAc and sat. aq. NaHCO3
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customThe residue was purified by column chromatography on silica gel (3% EtOAc/DCM to 40% EtOAc/DCM)

Sources & evidence

ORD record
ord-00ff55570b1246ee8e0b5024be3a24b9
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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