2-(Aminomethyl)-5-methylpyrazine → HCID 54724183, compound

HRID 1831998Notes

Reaction equation

HRID 1831998 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[NH2:10][CH2:11][C:12]1[N:13]=[CH:14][C:15]([CH3:18])=[N:16][CH:17]=1>O>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:10]([CH2:11][C:12]2[CH:17]=[N:16][C:15]([CH3:18])=[CH:14][N:13]=2)[C:4](=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724183HCID 54724183, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-hydroxy-6-methyl-2-pyrone (5.0 g, 0.04 mol) and 5-aminomethyl-2-methylpyrazine (5.0 g, 0.041 mol) in water (25.0 ml) was heated at 100° C. for 1 h under argon atmosphere. The reaction mixture was cooled, and filtered the yellow precipitate. It was washed with ethanol, and dried in vacuo to afford the title compound (5.8 g, 63%) as a pale yellow powder: 1H NMR (DMSO-d6/400 MHz) δ 10.43 (br, 1H), 8.38 (d, 2H, J=5.2 Hz), 5.77 (d, 1H, J=2.0 Hz), 5.58 (d, 1H, J=2.0 Hz), 4.92 (s, 2H), 2.24 (s, 3H), and 2.22 (s, 3H); ES MS m/z 232 (M+H) Step 2 3-Bromo-4-hydroxy-6-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyridin-2(1H)-one

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered the yellow precipitate
  3. washIt was washed with ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-fc480d1fa55546e29aa708fd2364fddd
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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