Hydrochloric Acid → 3-({5-Bromo-4-[(4-hydroxybutyl)amino]pyrimidin-2-yl}amino)phenol

HRID 970447Notes

Reaction equation

HRID 970447 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Br:9][C:10]1[C:11]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[N:12][C:13](Cl)=[N:14][CH:15]=1.Cl>C(#N)C.O1CCOCC1>[Br:9][C:10]1[C:11]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[N:12][C:13]([NH:1][C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 115683-AminophenolHCID 17986379HCID 17986379, compound

Product 1

HCID 179863513-({5-Bromo-4-[(4-hydroxybutyl)amino]pyrimidin-2-yl}amino)phenol

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A reaction mixture of 327 mg (3.0 mmol) of 3-aminophenol and 864 mg (3.1 mmol) of 4-(5-bromo-2-chloro-pyrimidin-4-ylamino)-butan-1-ol in 9 ml of acetonitrile is mixed with 0.75 ml of a 4 M solution of hydrochloric acid in dioxane, and it is stirred under reflux overnight. After the cooling, the reaction mixture is filtered, and the filtrate is completely concentrated by evaporation. The oil that is obtained is recrystallized from ethyl acetate/ethanol. The solid is filtered off and then dissolved in water. By adding triethylamine, the solution is made basic and extracted with ethyl acetate (2×). The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. 444 mg (1.2 mmol, corresponding to 40% of theory) of the product is obtained.

Workup

  1. temperatureunder reflux overnight
  2. filtrationAfter the cooling, the reaction mixture is filtered
  3. concentrationthe filtrate is completely concentrated by evaporation
  4. customThe oil that is obtained
  5. customis recrystallized from ethyl acetate/ethanol
  6. filtrationThe solid is filtered off
  7. dissolutiondissolved in water
  8. additionBy adding triethylamine
  9. extractionextracted with ethyl acetate (2×)
  10. dry with materialThe combined organic phases are dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated by evaporation
  13. custom444 mg (1.2 mmol, corresponding to 40% of theory) of the product is obtained

Sources & evidence

ORD record
ord-c7667976c60844648ea3726346fb0854
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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