Sodium Thiosulfate → 4-Chloro-6-ethyl-5-iodo-pyrimidin-2-ylamine

HRID 1907162Notes

Reaction equation

HRID 1907162 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.C1C(=O)N([I:18])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:18])=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 223243042-Amino-4-chloro-6-ethylpyrimidine

Product 1

HCID 585132964-Chloro-6-ethyl-5-iodo-pyrimidin-2-ylamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

25.0 g (159 mmol) 4-Chloro-6-ethyl-pyrimidin-2-ylamine in 1.0 L acetic acid is cooled to 0° C. and 36.0 g (159 mmol) NIS is added in one portion. 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 suspension stirred at RT for 60 minutes. The product is filtered off, washed with diethyl ether and dried in vacuo at 40° C. Yield: 40.3 g (90%). 1H NMR (DMSO-d6) δ: 7.2 (s, 2H), 2.7 (quart., 2H), 1.1 (tripl., 3H). HPLC-MS: tR=1.62 min., (M+H)=284.

Workup

  1. custom(18 h)
  2. filtrationThe formed precipitate is filtered off
  3. stirringthe suspension stirred at RT for 60 minutes
  4. filtrationThe product is filtered off
  5. washwashed with diethyl ether
  6. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-91aefa29b67a4a39b6aef1018a8b91ee
Source dataset
uspto-grants-2013_12
Patent number
US08598157B2

Reaction notes

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