6-Butyl-4-iodo-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine → 6-Butyl-5-(4-iodobenzyl)-2-methylpyrimidine-4-carbonitrile

HRID 1110056Notes

Reaction equation

HRID 1110056 reaction equation
[C:1]([Cu])#[N:2].[CH2:4]([C:8]1[N:13]=[C:12]([CH3:14])[N:11]=[C:10](I)[C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1)[CH2:5][CH2:6][CH3:7]>N1C=CC=CC=1.C(Cl)Cl>[CH2:4]([C:8]1[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:1]#[N:2])[C:9]=1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([I:23])=[CH:21][CH:22]=1)[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 190187966-Butyl-4-iodo-2-methyl-5-[(4-iodophenyl)methyl]pyrimidineHCID 178418546HCID 178418546, compound2×

Product 1

HCID 190188006-Butyl-5-(4-iodobenzyl)-2-methylpyrimidine-4-carbonitrileYield 87.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 800 mg (8.94 mmol) CuCN and 10 mL pyridine was heated to 110° C. until all of the CuCN went into solution (7 minutes). To this mixture was added a solution of 440 mg (0.894 mmol) 6-butyl-4-iodo-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine in 3 mL pyridine. After 5 minutes, the reaction mixture was cooled to room temperature, diluted with CH2Cl2, filtered through powdered cellulose flock, stripped of solvent in vacuo, and was medium pressure chromatographed on silica gel using 13% EtOAc/hexane to give 306 mg of the title compound, 87% yield. Rf 0.29 in 15% EtOAc/hexane, visualized by UV and ammonium molybdate/ceric sulfate stain; 1H-NMR (300 MHz, CDCl3): δ 7.63 (m, 2H), 6.84 (m, 2H), 4.16 (s, 2H), 2.73 (s, 3H), 2.68 (3 line m, 2 H), 1.53 (m, 2H), 1.31 (m, 2H), 0.87 (3 line m, 3H).

Workup

  1. customwent into solution (7 minutes)
  2. filtrationfiltered through powdered cellulose flock
  3. customchromatographed on silica gel using 13% EtOAc/hexane

Sources & evidence

ORD record
ord-0185c4ae38ca46eabe765af077339682
Source dataset
uspto-grants-1994_06
Patent number
US05324729

Reaction notes

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