Morpholine → 5-Chloro-4-morpholinopyridin-2-amine

HRID 384639Notes

Reaction equation

HRID 384639 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>CC(N(C)C)=O>[Cl:8][C:7]1[C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:3][C:4]([NH2:9])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 107733044,5-Dichloropyridin-2-amine

Product 1

HCID 596135085-Chloro-4-morpholinopyridin-2-amineYield 88.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4,5-dichloropyridin-2-amine (300 mg, 1.84 mmol) and morpholine (480 mg, 5.52 mmol) in DMA (3.6 mL) was heated at 200° C. for 60 minutes by microwave irradiation. The mixture was purified by ion exchange chromatography on SCX-II acidic resin (2 g) eluting with methanol, then 2M ammonia-methanol. The basic fractions were combined and solvent was evaporated. Flash chromatography on silica, eluting with ethyl acetate-hexane (1:1) gave 5-chloro-4-morpholinopyridin-2-amine as a colourless solid (347 mg, 88%).

Workup

  1. customThe mixture was purified by ion exchange chromatography on SCX-II acidic resin (2 g)
  2. washeluting with methanol
  3. customsolvent was evaporated
  4. washFlash chromatography on silica, eluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-8efb1946c2b04464a2ba6195faa05bf2
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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