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

HRID 886794Notes

Reaction equation

HRID 886794 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. 1H 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-356db36ee1f74436870cba3497dd3fc7
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

Loading…