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

HRID 361415Notes

Reaction equation

HRID 361415 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, 6 H), 2.0 (m, 1 H), 2.4 (s, 3 H), 4.0 (d, 2 H), 4.02 (s, 3 H), 7.3 (s, 1 H), 7.8 (s, 1 H); 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-5c3e0bcf16364091b5909209ee84f373
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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