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

HRID 1107462Notes

Reaction equation

HRID 1107462 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 (positive 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-2575bb51e8764c1194814d226ed472cc
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

Loading…