N-Iodosuccinimide → HCID 178517461, compound

HRID 1484847Notes

Reaction equation

HRID 1484847 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([OH:13])[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([I:21])C(=O)C1>C(O)(=O)C>[I:21][C:10]1[C:11]([OH:13])=[N:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178516486HCID 178516486, compound

Product 1

HCID 178517461HCID 178517461, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-phenylpyrimidin-4-ol (1.0 g, 5.8 mmol, 1 eq) in acetic acid (20 mL), was added NIS (1.3 g, 5.8 mmol, 1 eq), then heated at 50° C. for 1 h. The reaction solution was concentrated in vacuo and the residue was purified by silica gel chromatography (CH2Cl2/MeOH=97/3 as eluent) to obtain 5-iodo-2-phenylpyrimidin-4-ol (1.2 g, 69.8%) as a white solid. LC-MS (m/z): 298.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 7.35-7.51 (m, 3H), 8.10-8.18 (m, 2H), 8.43 (s, 1H), 13.32 (s, 1H).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography (CH2Cl2/MeOH=97/3 as eluent)

Sources & evidence

ORD record
ord-ad47b62b9d8442aa8024ed6ff4b687c9
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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