2-Amino-4-chloro-6-methylpyrimidine → 4-Chloro-5-iodo-6-methylpyrimidin-2-amine

HRID 1907161Notes

Reaction equation

HRID 1907161 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1.C1C(=O)N([I:17])C(=O)C1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:7]([I:17])=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1

Participants

6

Reactant 4

HCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 516892Sodium Bicarbonate

Product 1

HCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.0 g (70 mmol) 4-Chloro-6-methyl-pyrimidin-2-ylamine in 200 mL acetic acid is cooled to 0° C., 15.7 g (70 mmol) NIS is added and the reaction mixture is stirred at RT until conversion of the starting material is completed (18 h). An aqueous solution of 5% Na2S2O3 and 10% NaHCO3 is added until the mixture decolorizes. The formed precipitate is filtered off, taken up with water and the resulting suspension is stirred at RT for 1 h. The product is filtered off and dried in vacuo at 40° C. Yield: 15.2 g (81%). 1H NMR (CDCl3) δ: 5.2 (s, 2H), 2.6 (s, 3H). TLC (silica, 20% EtOAc in PE): Rf=0.50.

Workup

  1. custom(18 h)
  2. filtrationThe formed precipitate is filtered off
  3. stirringthe resulting suspension is stirred at RT for 1 h
  4. filtrationThe product is filtered off
  5. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-d48686eed4d94cc1b7f2f82534c913f8
Source dataset
uspto-grants-2013_12
Patent number
US08598157B2

Reaction notes

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