N-Iodosuccinimide → 5-Iodo-4-phenyl-pyrimidin-2-ylamine

HRID 1355686Notes

Reaction equation

HRID 1355686 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[I:14]N1C(=O)CCC1=O>C(O)(=O)C>[I:14][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 5987772-Amino-4-phenylpyrimidine

Product 1

HCID 185076485-Iodo-4-phenyl-pyrimidin-2-ylamineYield 16%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 500 mg (2.9 mmol) 2-amino-4-phenylpyrimidine in 38 ml acetic acid was added 689 mg (3.1 mmol) N-iodosuccinimide and stirring continued in the dark at room temperature for 16 h. The reaction mixture was then concentrated in vacuo and the residue partitioned between ether and water. The organic phase was then dried over sodium sulfate and concentrated in vacuo. Trituration in ether/ethyl acetate then afforded 138 mg (16%) 5-iodo-4-phenyl-pyrimidin-2-ylamine as a yellow crystalline solid. EI-MS m/e (%): 297 (M+, 100), 170 ([M—I]+, 38).

Workup

  1. customdark at room temperature
  2. customfor 16 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customthe residue partitioned between ether and water
  5. dry with materialThe organic phase was then dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dd93a8cc1a74d4ebdf2be3e794a37af
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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