Trimethylsilyldiazomethane → Methyl 2-(5-amino-4-methyl-2-pyridinyl)acetate

HRID 1502122Notes

Reaction equation

HRID 1502122 reaction equation
[CH3:1][C:2]1[C:7]([NH:8]C(=O)C(C)(C)C)=[CH:6][N:5]=[C:4]([CH2:15][C:16]([O:18][C:19](C)(C)C)=[O:17])[CH:3]=1.[Si](C=[N+]=[N-])(C)(C)C>Cl>[NH2:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 89619062Tert-butyl 2-(4-methyl-5-pivalamidopyridin-2-yl)acetate

Product 1

HCID 89619043Methyl 2-(5-amino-4-methyl-2-pyridinyl)acetate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyl 2-(4-methyl-5-pivalamidopyridin-2-yl)acetate (0.200 g, 0.653 mmol) was refluxed in hydrochloric acid 6N (10 ml) overnight. The reaction was concentrated then re-dissolved in MeOH (10 ml) and cooled to 0° C. then added TMS-diazomethane (0.653 ml, 1.305 mmol). When no SM was observed by TLC, the reaction was quenched with glacial acetic acid and concentrated. The residue was taken up with ethyl acetate and washed with NaHCO3. The organic layer was dried over NaSO4, filtered and evaporated to dryness. The residue was purified by chromatography using 40 g ISCO Redisep column and 5% MeOH/DCM solvent system to yield title compound.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthen re-dissolved in MeOH (10 ml)
  3. customthe reaction was quenched with glacial acetic acid
  4. concentrationconcentrated
  5. washwashed with NaHCO3
  6. dry with materialThe organic layer was dried over NaSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-9e8beb806e2f471f9342c5224b1224ab
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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