p-Toluenesulfonic acid → 8-Chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine

HRID 1186495Notes

Reaction equation

HRID 1186495 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1)[CH:3](OC)OC.[Cl:16][C:17]1[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][N:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C.O>[Cl:16][C:17]1[C:18]2[N:19]([C:2]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=3)=[CH:3][N:23]=2)[CH:20]=[CH:21][N:22]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2762242-Amino-3-chloropyrazineHCID 682265694-(1-Bromo-2,2-dimethoxy-ethyl)-2-methylsulfanyl-pyrimidine

Product 1

HCID 866709158-Chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The mixture of 4-(1-bromo-2,2-dimethoxy-ethyl)-2-methylsulfanyl-pyrimidine (from Example 43 supra) (7.5 g, 25.6 mmol), 3-chloropyrazin-2-amine (3.96 g, 30.7 mmol) and p-toluenesulfonic acid (1.594 g, 9.22 mmol) in the mix solvent of acetonitrile/water (120 mL:6 mL) was heated at reflux for 6 hours. The reaction mixture was concentrated and purified by chromatography (dichloromethane:methanol, 20:1) to give 8-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine as a white solid. (Yield 2.3 g, 32.4%). LC-MS: [M+H]+ 278.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by chromatography (dichloromethane:methanol, 20:1)

Sources & evidence

ORD record
ord-8ef8807185ea4589b1e0d1952ce42529
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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