Pyridine → Isobutyl (3-methoxy-5-methylpyrazin-2-yl)carbamate

HRID 1384194Notes

Reaction equation

HRID 1384194 reaction equation
[CH2:1]([O:5][C:6](Cl)=[O:7])[CH:2]([CH3:4])[CH3:3].[NH2:9][C:10]1[C:15]([O:16][CH3:17])=[N:14][C:13]([CH3:18])=[CH:12][N:11]=1.N1C=CC=CC=1>ClCCl>[CH3:17][O:16][C:15]1[C:10]([NH:9][C:6](=[O:7])[O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[N:11][CH:12]=[C:13]([CH3:18])[N:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62365Isobutyl chloroformateHCID 107018943-Methoxy-5-methyl-2-pyrazinamine

Product 1

HCID 10889995Isobutyl (3-methoxy-5-methylpyrazin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isobutylchloroformate (4.79 ml) was added to a stirred solution of 2-amino-3-methoxy-5-methylpyrazine (5 g) and pyridine (2.91 ml) in dichloromethane (10 ml) at ambient temperature. After 90 minutes the reaction mixture was diluted with dichloromethane (10 ml) and washed with 2M hydrochloric acid (3×20 ml), water (20 ml) and saturated sodium chloride solution (20 ml) and then dried (MgSO4). Volatile material was removed by evaporation to give a solid which was recrystallised from hexane to give isobutyl N-(3-methoxy-5-methylpyrazin-2-yl)carbamate (6.5 g); 1H NMR (CDCl3): 1.0 (d, 6H), 2.0 (m, 1H), 2.4 (s, 3H), 4.0 (d, 2H), 4.02 (s, 3H), 7.3 (s, 1H), 7.8 (s, 1H); mass spectrum (postive chemical ionisation (+ve CI)): 240 (M+H)+.

Workup

  1. washwashed with 2M hydrochloric acid (3×20 ml), water (20 ml) and saturated sodium chloride solution (20 ml)
  2. dry with materialdried (MgSO4)
  3. customVolatile material was removed by evaporation
  4. customto give a solid which
  5. customwas recrystallised from hexane

Sources & evidence

ORD record
ord-77bcb29d30d842be96d2e9c2a46af28a
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

Loading…