Formaldehyde → Methyl 2-(3-(dimethylamino)pyridin-2-yl)acetate

HRID 572920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572920
N[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:6][CH:7]=1.[CH2:13]=O.[BH3-][C:16]#[N:17].[Na+]>CO.CC(O)=O>[CH3:13][N:17]([CH3:16])[C:4]1[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:6][CH:7]=[CH:2][CH:3]=1

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 53659969Methyl 2-(5-aminopyridin-2-yl)acetate

Produkt 1

HCID 86719103Methyl 2-(3-(dimethylamino)pyridin-2-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To the solution of methyl 2-(5-aminopyridin-2-yl)acetate (600 mg, 3.6 mmol) and paraformaldehyde (578.3 mg, 19.3 mmol) in methanol (20 mL) was added NaBH3CN (1.2 g, 19.3 mmol) and AcOH (1 drop, cat.). The mixture was stirred at room temperature for 12 h. Then, the reaction was quenched with aqueous ammonium chloride and extracted with DCM. The organic layer was with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by a standard method to get desired product. LC-MS: m/z (M+H)=195.1

Aufarbeitung

  1. customThen, the reaction was quenched with aqueous ammonium chloride
  2. extractionextracted with DCM
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a standard method

Quellen und Nachweise

ORD-Eintrag
ord-9f231e1c87a347b29c1dee27118b16fd
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029531B2

Notizen zur Reaktion

Wird geladen…