Diisopropylethylamine → 6-bromo-N-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-amine

HRID 2400522Notes

Reaction equation

HRID 2400522 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([NH2:9])[CH:6]=[N:5]1)([CH3:3])[CH3:2].[Br:10][C:11]1[N:12]=[C:13](Br)[C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:10][C:11]1[N:12]=[C:13]([NH:9][C:7]2[CH:6]=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:8]=2)[C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 134698261-(Propan-2-yl)-1H-pyrazol-4-amineHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 866424656-bromo-N-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-amineYield 144.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of impure 1-isopropyl-1H-pyrazole-4-amine (2) (1.00 g), from above, 6,8-dibromoimidazo[1,2-a]pyrazine (3) (750 mg, 2.71 mmol), and N,N-diisopropylethylamine (526 mg, 4.16 mmol) in DMF (20 mL) was stirred at 100° C. for 3 h. After this time, the reaction was cooled to room temperature and poured into ice water (200 mL). The resulting suspension was filtered and the filter cake dried to a constant weight under vacuum to afford impure 6-bromo-N-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-amine (4) (1.26 g) as an off-white solid, which was used without further purification: 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.14 (s, 1H), 8.08 (s, 1H), 7.90 (s, 1H), 7.77 (s, 1H), 7.59 (s, 1H), 4.49 (m, 1H), 1.40 (d, 6H); ESI MS m/z 323.3 [M+H]+.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filter cake dried to a constant weight under vacuum

Sources & evidence

ORD record
ord-23022ceba3394a03845136627cf2a2ec
Source dataset
uspto-grants-2014_08
Patent number
US08796270B2

Reaction notes

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