Dichloromethane → (S)-4-(4,6-Dichloropyrimidin-2-yl)-3-methylmorpholine

HRID 1771521Notes

Reaction equation

HRID 1771521 reaction equation
Cl[C:2]1[C:3]([Cl:9])=[N:4][C:5](Cl)=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][NH:21]1.C(Cl)[Cl:27]>>[Cl:27][C:7]1[CH:2]=[C:3]([Cl:9])[N:4]=[C:5]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][C@@H:20]2[CH3:19])[N:6]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 72942068(S)-4-(4,6-Dichloropyrimidin-2-yl)-3-methylmorpholine

Procedure

To a solution of trichloropyrimidine (5.04 g, 27.3 mol) in DCM (50 mL) cooled to 0° C. was added DIPEA (4.79 mL, 27.3 mol), followed by 3-(S)-methylmorpholine (3.11 g, 30.5 mol) dropwise. The reaction mixture was allowed to warm to RT and stirred for 3 h wherupon it was diluted with DCM, washed with water and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (5-10% EtOAc in petroleum ether (40-60)) to yield the two isomers.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography (5-10% EtOAc in petroleum ether (40-60))
  6. customto yield the two isomers

Sources & evidence

ORD record
ord-a24d6938049f435f813d262d60333313
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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