Hydrochloric Acid → [4-(2-Amino-6-chloro-pyrimidin-4-yl-amino)-phenyl]-methanol

HRID 28563

Reaction equation

HRID 28563 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1.C(N(CC)C(C)C)(C)C.Cl>C(O)C>[NH2:9][C:4]1[N:3]=[C:2]([NH:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=2)[CH:7]=[C:6]([Cl:8])[N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 655222-Amino-4,6-dichloropyrimidineHCID 693314-Aminobenzyl alcoholHCID 81531Diisopropylethylamine

Product 1

HCID 86004324[4-(2-Amino-6-chloro-pyrimidin-4-yl-amino)-phenyl]-methanolYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,6-dichloro-pyrimidin-2-yl-amine (6.6 g, 40 mmol), 4-aminobenzyl alcohol (8.0 g, 65 mmol) and N,N-diisopropylethylamine (15 ml) in ethanol (200 ml) was heated under reflux for 72 hours. Concentration under reduced pressure provided a solid which was stirred with 1.0 M hydrochloric acid (200 ml) for 1 hour, filtered, dried under reduced pressure, stirred with ethyl acetate (200 ml) for 2 hours, filtered, and dissolved in methanol (300 ml). Aqueous sodium carbonate solution (1.0 M, 50 ml) was added. After stirring for 2 hours, volatiles were evaporated under reduced pressure and water (200 ml) was added. Filtration and drying provided [4-(2-amino-6-chloro-pyrimidin-4-yl-amino)-phenyl]-methanol (6.3 g, 63% yield) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 hours
  3. concentrationConcentration under reduced pressure
  4. customprovided a solid which
  5. filtrationfiltered
  6. customdried under reduced pressure
  7. filtrationfiltered
  8. dissolutiondissolved in methanol (300 ml)
  9. additionAqueous sodium carbonate solution (1.0 M, 50 ml) was added
  10. stirringAfter stirring for 2 hours
  11. customvolatiles were evaporated under reduced pressure and water (200 ml)
  12. additionwas added
  13. filtrationFiltration
  14. customdrying

Sources & evidence

ORD record
ord-753ba51b07e845fc9cfead58758f27e0
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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