Morpholine → HCID 23064218, compound

HRID 1504777Notes

Reaction equation

HRID 1504777 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>>[CH3:8][C:6]1[N:5]=[C:4]([NH2:9])[CH:3]=[C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 190505094-Chloro-6-methylpyridin-2-amine

Product 1

HCID 23064218HCID 23064218, compound

Conditions

Temperature
150 °C

Procedure

To 4-chloro-6-methylpyridin-2-amine (150 mg, 1.05 mmol) in a nitrogen purged vial was added morpholine (0.917 mL, 10.5 mmol). The reaction mixture was sealed and heated at 150° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (10 mL) and washed with aqueous saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-10% methanol/DCM with 1% ammonium hydroxide, linear gradient) to give 6-methyl-4-morpholinopyridin-2-amine. MS ESI calc'd. for C10H16N3O [M+H]+ 194. found 194. 1H NMR (500 MHz, DMSO-d6) δ 6.00 (s, 1H), 5.62 (s, 1H), 5.42 (s, 2H), 3.63 (m, 4H), 3.08 (m, 4H), 2.08 (s, 3H).

Workup

  1. customThe reaction mixture was sealed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. washwashed with aqueous saturated sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (0-10% methanol/DCM with 1% ammonium hydroxide, linear gradient)

Sources & evidence

ORD record
ord-8c64364ed4fb4022aa3b9dcac56042d1
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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