1-Ethyl-1h-pyrazol-4-amine → 5-Bromo-3-(1-ethyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one

HRID 1918863Notes

Reaction equation

HRID 1918863 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4]1)[CH3:2].Br[C:10]1[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=[C:14]([Br:16])[N:15]=1>>[Br:16][C:14]1[N:15]=[C:10]([NH:8][C:6]2[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=2)[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=1

Participants

3

Reactant 2

HCID 70186401-Ethyl-1h-pyrazol-4-amineHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Product 1

HCID 580437415-Bromo-3-(1-ethyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-oneYield 75.3%

Procedure

Following Example 111b, reaction of 1-ethyl-1H-pyrazol-4-amine (500 mg, 4.50 mmol) and 3,5-dibromo-1-methylpyrazin-2(1H)-one (1.33 g, 4.95 mmol) afforded a 75% yield (1.01 g) of 131b as an off-white solid: mp 237-239° C.; 1H NMR (300 MHz, DMSO-d6) d 9.90 (s, 1H), 8.02 (s, 1H), 7.73 (s, 1H), 7.20 (s, 1H), 4.11 (q, 2H, J=7.5 Hz), 3.41 (s, 3H), 1.34 (t, 3H, J=7.3 Hz); MS (ESI+) m/z 298.0 (M+H).

Sources & evidence

ORD record
ord-b90ae97a47464e048e966db7ae9c3195
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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