Methanol → 4-Chloro-5-iodo-6-methylpyrimidin-2-amine

HRID 243150Notes

Reaction equation

HRID 243150 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1.CO.[I:12]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[C:7]([I:12])=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 120273N-Iodosuccinimide

Product 1

HCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amineYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-6-methylpyrimidin-2-ylamine (5 g, 0.04 mol) was suspended in acetonitrile (50 mL) and methanol (50 mL) and N-iodosuccinimide (12 g, 0.05 mol, 1.5 equiv.) added to the resulting mixture. The mixture was heated to 60° C. under a nitrogen atmosphere for 3 h. A solid precipitated in the resulting brown mixture and was isolated by filtration and washed with cyclohexane to give a white crystalline solid 6 g, 65%. Additional product (˜2.5 g) was present in the mother liquors. LCMS m/e 270 35Cl/272 37Cl (M++1);

Workup

  1. customA solid precipitated in the resulting brown mixture
  2. customwas isolated by filtration
  3. washwashed with cyclohexane

Sources & evidence

ORD record
ord-ce675c4bb9cf4fa3b500a612e278c56f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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