Iodine chloride → N-ethyl-5-iodo-6-methyl-2-(methylthio)pyrimidin-4-amine

HRID 1893880Notes

Reaction equation

HRID 1893880 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([S:11][CH3:12])[N:5]=1)[CH3:2].[I:13]Cl>CO>[CH2:1]([NH:3][C:4]1[C:9]([I:13])=[C:8]([CH3:10])[N:7]=[C:6]([S:11][CH3:12])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 57606957N-Ethyl-6-methyl-2-(methylsulfanyl)pyrimidin-4-amine

Product 1

HCID 57606954N-ethyl-5-iodo-6-methyl-2-(methylthio)pyrimidin-4-amineYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of N-ethyl-6-methyl-2-(methylthio)pyrimidin-4-amine (20 g, 121.6 mmol) in methanol was added iodine monochloride (26.58 g, 163.7 mmol) in small portions at 0° C. Then the reaction mixture was stirred overnight. After evaporation of solvent, the residue was triturated with acetone. The product N-ethyl-5-iodo-6-methyl-2-(methylthio)pyrimidin-4-amine (25.2 g, 75% yield) was collected by filtration. 1H NMR (400 MHz, CDCl3): δ 5.37 (bs, 1H), 3.52 (q, J=7.2 Hz, 1H), 2.50 (s, 3H), 1.26 (t, J=7.2 Hz, 3H).

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was triturated with acetone

Sources & evidence

ORD record
ord-549d581f11cb4eae893c8ad00fcfbef3
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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