Imidazole → HCID 89561451, compound

HRID 530124Notes

Reaction equation

HRID 530124 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][CH:13]([CH3:17])[CH2:14][CH2:15][NH2:16].N1C=CN=C1>ClC(Cl)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:16][CH2:15][CH2:14][CH:13]([CH3:17])[CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7894IsoamylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 89561451HCID 89561451, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2,4-dichloro-5-nitropyrimidine (13.8 g, 99.28 mmol) and 3-methylbutan-1-amine (7.0 g, 80.45 mmol) in dichloroethane (150 mL) was added imidazole (3.78 g, 55.58 mmol) at 0° C., the resulting mixture was stirred at 0° C. for 30 minutes then stirred at rt for 16 h. The solvent was removed under reduced pressure to give a crude residue was purified by silica gel column chromatography (eluent: 2% ethyl acetate in hexane) to yield 5.5 g of the desired compound. 1H NMR (CDCl3, 300 MHz) δ 0.98 (d, J=6.8 Hz, 6H), 1.56-1.81 (m, 3H), 3.60-3.75 (m, 2H), 8.40 (br s, 1H), 9.01 (s, 1H); MS m/z 245[M+H+].

Workup

  1. stirringthen stirred at rt for 16 h
  2. customThe solvent was removed under reduced pressure
  3. customto give a crude residue
  4. customwas purified by silica gel column chromatography (eluent: 2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ff6f4157c8134ad8b9633f216c1badbc
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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