Dimethylformamide → 5-Methyl-2,4-bis(4-cyanophenyl)pyrimidine

HRID 1452024Notes

Reaction equation

HRID 1452024 reaction equation
[CH3:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[Cu][C:23]#[N:24].[CH3:25][N:26](C=O)C>>[CH3:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][C:18]([C:23]#[N:24])=[CH:17][CH:16]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:25]#[N:26])=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 107161785-Methyl-2,4-bis(4-bromophenyl)pyrimidineHCID 178418546HCID 178418546, compound

Product 1

HCID 105658625-Methyl-2,4-bis(4-cyanophenyl)pyrimidineYield 48%

Procedure

A mixture of 5-methyl-2,4-bis(4-bromophenyl)pyrimidine (8.08 g, 0.02 mole) and copper(I) cyanide (4.45 g, 0.05 mole) in 35 mL dry DMF is refluxed under nitrogen for 40 hr (TLC monitored), the excess DMF is distilled under vacuum using a water aspirator. The residual mass is diluted with water and poured into 200 mL 10% NaCN solution, stirred for 2-3 hr, filtered, washed thoroughly with water, dried and subjected to soxlet extraction using acetone. The acetone is distilled and the residue dissolved into 75 mL CHCl3 and chromatographed over an aluminumoxide column, eluted with ether to 80:20 CHCl3: ether to yield a white crystalline solid (2.8 g, 48%), mp 194°-195° C.

Workup

  1. temperatureis refluxed under nitrogen for 40 hr (TLC monitored)
  2. distillationthe excess DMF is distilled under vacuum
  3. additionThe residual mass is diluted with water
  4. additionpoured into 200 mL 10% NaCN solution
  5. filtrationfiltered
  6. washwashed thoroughly with water
  7. customdried
  8. extractionextraction
  9. distillationThe acetone is distilled
  10. dissolutionthe residue dissolved into 75 mL CHCl3
  11. customchromatographed over an aluminumoxide column
  12. washeluted with ether to 80:20 CHCl3

Sources & evidence

ORD record
ord-9b64551a584b4a929226bf34b86de204
Source dataset
uspto-grants-1997_02
Patent number
US05606058

Reaction notes

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