Morpholine → 4-(2,6-Dichloro-5-fluoropyrimidin-4-yl)morpholine

HRID 573989Notes

Reaction equation

HRID 573989 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:13]=[C:12](Cl)[C:11]([F:15])=[C:10]([Cl:16])[N:9]=1>C(O)C>[Cl:7][C:8]1[N:13]=[C:12]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[C:11]([F:15])=[C:10]([Cl:16])[N:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 133889932,4,6-Trichloro-5-fluoropyrimidine

Product 1

HCID 866441264-(2,6-Dichloro-5-fluoropyrimidin-4-yl)morpholineYield 53.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of morpholine (1.5 mL, 17.05 mmol) in ethanol (25 mL) was added to a cooled (−20° C.) solution of 2,4,6-trichloro-5-fluoropyrimidine (3.00 g, 14.93 mmol) in ethanol (150 mL) and the resulting mixture was stirred at −20° C. for 30 minutes and at ambient temperature for 3 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between water and methylene chloride. The organic layer was separated, dried and the solvent evaporated under reduced pressure. The resulting white solid was triturated with ethanol, then filtered and dried to give the title compound (2.0 g, 53%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water and methylene chloride
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent evaporated under reduced pressure
  6. customThe resulting white solid was triturated with ethanol
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-64f952acd6d84900bfc76b6b55c02925
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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