Phosphorus oxychloride → 6-Butyl-4-chloro-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine

HRID 373962Notes

Reaction equation

HRID 373962 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[NH:8][C:7](=O)[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].O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([Cl:23])[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

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 1360140486-Butyl-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine-4(3H)-one

Product 1

HCID 190187956-Butyl-4-chloro-2-methyl-5-[(4-iodophenyl)methyl]pyrimidineYield 75%

Procedure

A solution of 485 mg (1.27 mmol) 6-butyl-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine-4(3H)-one in 7 mL POCl3 was refluxed for 60 minutes. After cooling to room temperature, excess POCl3 was stripped off in vacuo. The crude product was partitioned between CH2Cl2 and a mixture of brine and NaHCO3. The organic layer was removed and the aqueous layer was extracted three more times with CH2Cl2. The combined organic material was dried over MgSO4, stripped of solvent in vacuo, then was medium pressure chromatographed on silica gel using 10% EtOAc/hexane to give 380 mg of 6-butyl-4-chloro-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine, 75% yield.

Workup

  1. customThe crude product was partitioned between CH2Cl2
  2. additiona mixture of brine and NaHCO3
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted three more times with CH2Cl2
  5. dry with materialThe combined organic material was dried over MgSO4
  6. customchromatographed on silica gel using 10% EtOAc/hexane

Sources & evidence

ORD record
ord-558004552347448b94808c02e829812d
Source dataset
uspto-grants-1992_11
Patent number
US05166206

Reaction notes

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