2,4-Dichloropyrimidine → (S)-4-(2-Chloropyrimidin-4-yl)-3-methylmorpholine

HRID 1771523Notes

Reaction equation

HRID 1771523 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][C@H:19]1[CH2:24][O:23][CH2:22][CH2:21][NH:20]1>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][C@@H:19]2[CH3:18])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 72942067(S)-4-(2-Chloropyrimidin-4-yl)-3-methylmorpholineYield 91%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-dichloropyrimidine (5.00 g, 0.034 mol) and DIPEA (8.00 mL, 0.046 mol) in 2-propanol (60 mL) at 0° C. was added (S)-3-methylmorpholine (3.73 g, 0.037 mol) dropwise. The reaction mixture was stirred at 0° C. for 30 min and then allowed to warm to RT and stirred for a further 16 h. Solvent was removed in vacuo and the residue was then partitioned between water and EtOAc. The phases were separated and the organic layer washed with brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo to yield a yellow oil (6.54 g, 91%).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for a further 16 h
  3. customSolvent was removed in vacuo
  4. customthe residue was then partitioned between water and EtOAc
  5. customThe phases were separated
  6. washthe organic layer washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-34fac89d131940a6b17ba0653a082f46
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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