Sodium Iodide → 6-Butyl-4-iodo-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine

HRID 373963Notes

Reaction equation

[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7](Cl)[C:6]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4].[IH:21].[Na+].[I-]>CC(C)=O>[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([I:21])[C:6]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 380 mg (0.947 mmol) 6-butyl-4-chloro-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine in 10 mL acetone were added 0.119 mL 57% HI (0.900 mmol) and 851 mg (5.68 mmol) NaI. The mixture was warmed to 40° C. for 2.5 hours. As the reaction proceeds, NaCl can be seen precipitating out of solution. The mixture was diluted with brine and saturated NaHCO3 solution. The mixture was extracted 3 times with ether. The combined organic material was dried over MgSO4 and decolorized with activated charcoal, was stripped of solvent in vacuo, then was medium pressure chromatographed on silica gel using 10% EtOAc/hexane to give 440 mg of 6-butyl-4-iodo-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine, 94% yield.

Workup

customNaCl can be seen precipitating out of solution
additionThe mixture was diluted with brine and saturated NaHCO3 solution
extractionThe mixture was extracted 3 times with ether
dry with materialThe combined organic material was dried over MgSO4
customchromatographed on silica gel using 10% EtOAc/hexane

Sources & evidence

ORD record: ord-ba47aa0b4c304e65a3971af76ba70c68
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166206

Reaction notes

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