Morpholine → 4-(6-Chloro-2-methylpyrimidin-4-yl)morpholine

HRID 249691Notes

Reaction equation

HRID 249691 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([Cl:9])[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 202455714-(6-Chloro-2-methylpyrimidin-4-yl)morpholineYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

The crude 2-methyl-4,6-dichloropyrimidine (41.8 g; 256 mmol) was dissolved in dichloromethane (200 mL) and chilled to −78° C. in an inert atmosphere. Morpholine (48 g; 550 mol) dissolved in dichloromethane (100 mL) was added slowly. The reaction was allowed to warm to room temperature while stirring overnight. The organic layer was washed with saturated ammonium chloride (2×100 mL), dried with sodium sulfate, and evaporated to give 2-methyl-4-chloro-6-morpholino-pyrimidine (48.5 g; 227 mmol).

Workup

  1. additionwas added slowly
  2. temperatureto warm to room temperature
  3. washThe organic layer was washed with saturated ammonium chloride (2×100 mL)
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c62317b1094f4bb3b735a33136a7e4a3
Source dataset
uspto-grants-2011_01
Patent number
US07863270B2

Reaction notes

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