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

HRID 1454761Notes

Reaction equation

HRID 1454761 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)SC)[C:3]=1[NH2:4].[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][C:12]2[N:13]=[C:14]([O:20][CH3:21])[CH:15]=[C:16]([O:18][CH3:19])[N:17]=2)[C:3]=1[NH2:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 575309642-Chloro-6-[1-(4,6-dimethoxypyrimidin-2-yl)-1-methylthiomethyl]aniline

Product 1

HCID 575309582-Chloro-6-[(4,6-dimethoxypyrimidin-2-yl)methyl]anilineYield 93.3%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To 10 ml of a methanol solution of 2-chloro-6-[1-(4,6-dimethoxypyrimidin-2-yl)-1-methylthiomethyl]aniline 0.6 g (1.84 mmol) and 0.88 g (3.68 mmol) of nickel(II) chloride hexahydrate, 0.28 g (7.37 mmol) of sodium borohydride was added at 0-10° C. and the reaction solution was stirred at room temperature for 2 hours. After the reaction solution was distilled off under reduced pressure, aqueous ammonia and dichloromethane were added and the insoluble matter was filtered off. The organic layer was separated and the water layer was further extracted three times with dichloromethane. After the organic layer had been washed with water and dried, dichloromethane was distilled off under reduced pressure and the obtained crystals were washed with n-hexane to obtain the objective 2-chloro-6-[(4,6-dimethoxypyrimidin-2-yl)methyl]aniline 0.48 g (yield 93%) as white crystals.

Workup

  1. distillationAfter the reaction solution was distilled off under reduced pressure, aqueous ammonia and dichloromethane
  2. additionwere added
  3. filtrationthe insoluble matter was filtered off
  4. customThe organic layer was separated
  5. extractionthe water layer was further extracted three times with dichloromethane
  6. washAfter the organic layer had been washed with water
  7. customdried
  8. distillationdichloromethane was distilled off under reduced pressure
  9. washthe obtained crystals were washed with n-hexane

Sources & evidence

ORD record
ord-3113ff7f272645729c7b1f7a4da8b950
Source dataset
uspto-grants-2009_01
Patent number
US07482308B2

Reaction notes

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