Iodine chloride → 5-Iodo-N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine

HRID 1893898Notes

Reaction equation

HRID 1893898 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([S:12][CH3:13])[N:6]=1)([CH3:3])[CH3:2].[I:14]Cl>CO>[I:14][C:10]1[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]([S:12][CH3:13])=[N:8][C:9]=1[CH3:11]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 55250529N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine

Product 1

HCID 576069565-Iodo-N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a crude solution of N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine (44.6 g, 224 mmol), prepared using analogous procedures as described in Example 1, in 400 mL of methanol was added ICl (40.0 g, 246 mmol) in small portions at room temperature. The reaction mixture was then stirred at for 3 h monitoring by LC/MS. After evaporation of solvent by rotary evaporator, the residue was triturated with acetone to yield 5-iodo-N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine. NMR (400 MHz, CDCl3) δ 6.37 (br m, 1H), 4.47 (m, 1H), 2.78 (s, 3H), 2.67 (s, 3H), 1.41 (d, J=6.4, 6H).

Workup

  1. customAfter evaporation of solvent
  2. customby rotary evaporator
  3. customthe residue was triturated with acetone

Sources & evidence

ORD record
ord-bd4eb65ea4ed437db5d461b4ea192c93
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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