Hydrochloric Acid → 2-Chloro-5-(pyrimidin-2-ylamino)phenol

HRID 1474014Notes

Reaction equation

HRID 1474014 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:16])=[C:13]([OH:15])[CH:14]=1.Cl>CCO.CCOC(C)=O>[Cl:16][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:14][C:13]=1[OH:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 744042-Chloropyrimidine2×HCID 806765-Amino-2-chlorophenol

Product 1

HCID 594749452-Chloro-5-(pyrimidin-2-ylamino)phenolYield 36.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloropyrimidine (1.5 g, 13.3 mmol), 5-amino-2-chlorophenol (318 mg, 2.2 mmol) and 37% HCl solution (1.1 mL, 13.3 mmol) in 10% aqueous EtOH solution (10 mL) was stirred at 90° C. for 24 h. Afterwards, 2-chloropyrimidine (1.5 g, 13.3) was added and after 24 h, the reaction mixture was diluted with AcOEt and washed with 5% aqueous K2CO3 solution and brine. The organic phase was dried over Na2SO4, concentrated and the crude product (179 mg, 36% yield) was used for the next step without additional purification.

Workup

  1. washwashed with 5% aqueous K2CO3 solution and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f5ea4274a71e4aa3a43694f2735d310f
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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