Sodium Iodide → {5-[(2-Chloro-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-methyl-amine

HRID 1726912Notes

Reaction equation

HRID 1726912 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH:12][CH3:13])=[N:6][C:7]([S:10][CH3:11])=[N:8][CH:9]=1.[I-].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[NH2:26]>C(#N)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[NH:26][CH2:3][C:4]1[C:5]([NH:12][CH3:13])=[N:6][C:7]([S:10][CH3:11])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 226912-Chloro-5-nitroanilineHCID 21988143(5-Chloromethyl-2-methylsulfanyl-pyrimidin-4-yl)-methyl-amine hydrochloride

Product 1

HCID 68700288{5-[(2-Chloro-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-methyl-amineYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

15.85 g (5-Chloromethyl-2-methylsulfanyl-pyrimidin-4-yl)-methyl-amine hydrochloride, 1.979 g sodium iodide, and 34.49 mL N—N-diisopropylethylamine were solved in 150 ml acetonitrile and cooled to 0° C. 17.085 g 2-Chloro-5-nitro-phenylamine dissolved in 150 ml acetonitrile were added slowly under stirring. The reaction mixture was stirred at room temperature for 48 hrs, then the solvent was evaporated. The residue was solved in a mixture of water/acetic acid ethyl ester (1:1), stirred and the crystalline product was isolated by filtration and dried for 48 h under vacuum at 40° C. The two phases of the mother liquor were separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, the solvent was evaporated and the residue was rubbed with diethyl ether. Both residues were combined and gave of the title product in 97% yield.

Workup

  1. additionwere added slowly
  2. stirringThe reaction mixture was stirred at room temperature for 48 hrs
  3. customthe solvent was evaporated
  4. additionThe residue was solved in a mixture of water/acetic acid ethyl ester (1:1)
  5. stirringstirred
  6. customthe crystalline product was isolated by filtration
  7. customdried for 48 h under vacuum at 40° C
  8. customThe two phases of the mother liquor were separated
  9. extractionthe aqueous phase was extracted with dichloromethane
  10. dry with materialdried over sodium sulfate
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c6e4527ee27f491b96e86471f678b9b3
Source dataset
uspto-grants-2009_02
Patent number
US07494993B2

Reaction notes

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