Carbamic acid, N-[(2,4-dimethoxy-6-methyl-3-pyridinyl)methyl]-, 1,1-dimethylethyl ester → HCID 178492315, compound

HRID 2206609Notes

Reaction equation

HRID 2206609 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:10]([O:18]C)=[N:11][C:12]([CH3:17])=[CH:13][C:14]=1[O:15][CH3:16])(C)(C)C>Cl.CCO>[NH2:7][CH2:8][C:9]1[C:10]([OH:18])=[N:11][C:12]([CH3:17])=[CH:13][C:14]=1[O:15][CH3:16]

Participants

4

Reactant 1

HCID 117689033Carbamic acid, N-[(2,4-dimethoxy-6-methyl-3-pyridinyl)methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 178492315HCID 178492315, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

tert-butyl((2,4-dimethoxy-6-methylpyridin-3-yl)methyl)carbamate (83 g, 294 mmol) was dissolved in 4 N HCl/H2C (830 ml). Then the mixture was refluxed for 4.5 h. (The reaction mixture was monitored by MS spectrum to make sure the methyl group at 2-position de-protect completely.) After the reaction completed, the mixture was concentrated under vacuum to give a brown oil. The oil was suspended in EtOH (300 ml) for 15 min to give a yellow precipitate. The precipitate was filtered, washed with ethanol (100 ml) and MTBE (100 ml) and dried under high vacuum to give 38 g of fraction 1 3-(aminomethyl)-4-methoxy-6-methylpyridin-2-ol (Purity 98% by LCMS, yield 63%) as a yellow powder. In the meantime, the filtration from fraction 1 was concentrated under vacuum and the residue was solidified by ethanol (100 ml). The precipitate was filtered, washed with ethanol (100 ml) and MTBE (100 ml) and dried under high vacuum to give 20 g of fraction 2 3-(aminomethyl)-4-methoxy-6-methylpyridin-2-ol (Purity 94% by LCMS, yield 33%) as a yellow powder.

Workup

  1. temperatureThen the mixture was refluxed for 4.5 h. (The reaction mixture
  2. concentrationthe mixture was concentrated under vacuum
  3. customto give a brown oil
  4. customto give a yellow precipitate
  5. filtrationThe precipitate was filtered
  6. washwashed with ethanol (100 ml) and MTBE (100 ml)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-6f88d0e3772b46fcb63d619b099cd750
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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