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

HRID 572920Notes

Reaction equation

HRID 572920 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-9f231e1c87a347b29c1dee27118b16fd
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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