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Hydrochloric Acid → 5-Bromo-n4-isopropyl-n2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine

HRID 548948
Notes
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Reaction equation

HRID 548948 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 15693Benzenamine, 3-(methylthio)-HCID 516892Sodium BicarbonateHCID 24903516(5-Bromo-2-chloropyrimidin-4-yl)isopropylamine

Product 1

HCID 596831645-Bromo-n4-isopropyl-n2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent
HCID 312751,4-DioxaneSolvent

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

  1. temperatureAfter cooling
  2. extractionIt is extracted with ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customRemoval of the solvent and recrystallization of the residue from ethyl acetate/hexane 9/1
  6. customresult in 0.17 g (79% of theory) of the product

Sources & evidence

ORD record
ord-064e26cfaf6c47fa871be0303581f292
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943629B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes