Sodium borohydride → 2-Chloro-6-[1-(4,6-dimethoxypyrimidin-2-yl)ethyl]aniline

HRID 1678043Notes

Reaction equation

HRID 1678043 reaction equation
CS[C:3]([C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[NH2:12])[CH3:4].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:12][C:6]1[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=1[CH:3]([C:13]1[N:14]=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[N:18]=1)[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58970390HCID 58970390, compound

Product 1

HCID 589703892-Chloro-6-[1-(4,6-dimethoxypyrimidin-2-yl)ethyl]anilineYield 82%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-{1-methylthio-1-(2-amino-3-chlorophenyl)ethyl}-4,6-dimethoxypyrimidine 3 g (8.8 mmol) in 100 ml methanol, nickel (II) chloride hexahydrate 4.2 g (17.7 mmol) was added at 0° C. and the mixture was stirred for 30 minutes. Then, at the same temperature, sodium borohydride 1.35 g (35 mmol) was added little by little thereto. The solution was stirred at room temperature for 1 hour and then the solvent was distilled off. 2N-hydrochloric acid was added to the residue and then 28% aqueous ammonia was added and the mixture was extracted with ethyl acetate. The organic layer washed with an aqueous solution of sodium hydroxide and the solvent was distilled off. After washing with hexane, the deposited crystals were filtered to obtain 2-{1-(2-amino-3-chlorophenyl)ethyl}-4,6-dimethoxypyrimidine 2.12 g (82%).

Workup

  1. stirringThe solution was stirred at room temperature for 1 hour
  2. distillationthe solvent was distilled off
  3. addition2N-hydrochloric acid was added to the residue
  4. addition28% aqueous ammonia was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer washed with an aqueous solution of sodium hydroxide
  7. distillationthe solvent was distilled off
  8. washAfter washing with hexane
  9. filtrationthe deposited crystals were filtered

Sources & evidence

ORD record
ord-91078162961246a188fd8a238288884b
Source dataset
uspto-grants-2011_08
Patent number
US08008484B2

Reaction notes

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