Water → 4-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amine

HRID 79436

Reaction equation

HRID 79436 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][C:10]1([CH3:17])[O:14][CH:13]([CH2:15][OH:16])[CH2:12][O:11]1.[Na].O>ClCCl>[CH3:9][C:10]1([CH3:17])[O:14][CH:13]([CH2:15][O:16][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH2:12][O:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 7528SolketalHCID 5818662-Amino-4-chloropyridineHCID 5360545Sodium

Product 1

HCID 509875954-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
145 °C

Procedure

A sealed tube containing 4-chloro-2-pyridinamine (4 g, 31.2 mmol), (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (8.4 g, 60.6 mmol), and sodium (1.46 g, 63.5 mmol) was heated at 145° C. for 8 hours. The mixture was cooled to ambient temperature; water (25 mL) and dichloromethane (50 mL) were added. The organic phase was separated, dried with sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica-gel to give 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amine as a pale yellow solid (5.6 g).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe organic phase was separated
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on silica-gel

Sources & evidence

ORD record
ord-5231720e43f441fda1d0c65964eaca65
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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