Hydrochloric Acid → 5-Bromo-n4-isopropyl-n2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine
Reaction equation
Cl.[Br:2][C:3]1[C:4]([NH:10][CH:11]([CH3:13])[CH3:12])=[N:5][C:6](Cl)=[N:7][CH:8]=1.[CH3:14][S:15][C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C(#N)C>[Br:2][C:3]1[C:4]([NH:10][CH:11]([CH3:13])[CH3:12])=[N:5][C:6]([NH:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([S:15][CH3:14])[CH:17]=2)=[N:7][CH:8]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
0.14 ml of a 4 molar solution of hydrogen chloride in dioxane and 0.17 ml of water are added to a solution of 0.152 g (0.61 mmol) of (5-bromo-2-chloropyrimidin-4-yl)-isopropylamine and 0.077 g (0.55 mmol) of 3-methylsulphanylphenylamine in 2 ml of acetonitrile, and the mixture is then stirred at 50° C. for 24 hours. After cooling, the mixture is added to saturated sodium bicarbonate solution. It is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate. Removal of the solvent and recrystallization of the residue from ethyl acetate/hexane 9/1 result in 0.17 g (79% of theory) of the product.
Workup
- temperatureAfter cooling
- extractionIt is extracted with ethyl acetate
- washThe combined organic phases are washed with saturated sodium chloride solution
- dry with materialdried over sodium sulphate
- customRemoval of the solvent and recrystallization of the residue from ethyl acetate/hexane 9/1
- customresult in 0.17 g (79% of theory) of the product
Sources & evidence
- ORD record
- ord-064e26cfaf6c47fa871be0303581f292
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943629B2
Reaction notes
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