Diiodomethane → N-(2-iodopyrimidin-5-yl)-2-methyl-5-nitrobenzamide

HRID 453356Notes

Reaction equation

HRID 453356 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[CH3:19])=[CH:4][N:3]=1.C(I)[I:22].CCOC(C)=O>C1COCC1.[Cu]I>[I:22][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[CH3:19])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 8857Ethyl AcetateHCID 16118604N-(2-aminopyrimidin-5-yl)-2-methyl-5-nitrobenzamide

Product 1

HCID 24823735N-(2-iodopyrimidin-5-yl)-2-methyl-5-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

N-(2-Aminopyrimidin-5-yl)-2-methyl-5-nitrobenzamide [prepared according to Specific Method 1] (200 mg, 0.732 mmol), CuI (140 mg, 0.732 mmol) and CH2I2 (0.30 mL, 3.73 mmol) were taken up in THF (3.7 mL) in a 16×100 mm resealable pyrex tube. The tube was sealed and the mixture was heated at 70° C. for 2 h. After cooling to rt, the crude reaction mixture was taken up in 1:1 EtOAc:1N HCl and the layers were separated. The organics were washed with saturated NH4Cl then dried over Na2SO4. Purification by MPLC (Isco—100% EtOAc eluent) afforded N-(2-iodopyrimidin-5-yl)-2-methyl-5-nitrobenzamide as a pale yellow solid.

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling to rt
  3. customthe crude reaction mixture
  4. custom1N HCl and the layers were separated
  5. washThe organics were washed with saturated NH4Cl
  6. dry with materialthen dried over Na2SO4
  7. customPurification by MPLC (Isco—100% EtOAc eluent)

Sources & evidence

ORD record
ord-c2d7410d2b3d498fb98b8e06d48eb7c3
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

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