Sodium Hydroxide → 5-Iodo-6-methylpyrimidine-2,4-diamine

HRID 1939669Notes

Reaction equation

HRID 1939669 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[I:10]Cl.[OH-].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([I:10])=[C:4]([CH3:9])[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24640Iodine chlorideHCID 2297436-Methyl-2,4-pyrimidinediamine

Product 1

HCID 158557925-Iodo-6-methylpyrimidine-2,4-diamineYield 73.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of 8.0 grams (0.064 mole) of 2,4-diamino-6-methylpyrimidine in 30 mL of glacial acetic acid is stirred, and a solution of 13.5 grams (0.083 mole) of iodine monochloride in 20 mL of glacial acetic acid is added drop-wise during a 5 minute period. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 18 hours. After this time the reaction mixture is diluted with 100 mL of water and then is made basic with 10% aqueous sodium hydroxide. The mixture is then extracted with three 75 mL portions of ethyl acetate. The combined extracts are washed with one 75 mL portion of an aqueous solution saturated with sodium chloride. The organic layer is added with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 11.7 grams of 2,4-diamino-5-iodo-6-methylpyrimidine. The NMR spectrum is consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionThe mixture is then extracted with three 75 mL portions of ethyl acetate
  3. washThe combined extracts are washed with one 75 mL portion of an aqueous solution saturated with sodium chloride
  4. additionThe organic layer is added with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f4c66a3916b14636a052b06a4c557f50
Source dataset
uspto-grants-1997_12
Patent number
US05696259

Reaction notes

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