6-Chloronicotinoyl Chloride → N-(4-tert-Butyl-pyrimidin-2-yl)-6-chloro-nicotinamide

HRID 2190521Notes

Reaction equation

HRID 2190521 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][N:14]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>>[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([Cl:12])=[N:14][CH:15]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 27821656-Chloronicotinoyl ChlorideHCID 124506314-tert-Butylpyrimidin-2-amineHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 59318000N-(4-tert-Butyl-pyrimidin-2-yl)-6-chloro-nicotinamide

Procedure

N-(4-tert-Butyl-pyrimidin-2-yl)-6-chloro-nicotinamide was prepared from 4-tert-butyl-pyrimidin-2-ylamine (prepared as described in J. Org. Chem. 1977, 221) and 6-chloronicotinoyl chloride following a procedure similar to the one described in the synthesis of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide, above. The product was isolated after silica gel purification with 20-40% EtOAc in hexanes gradient followed by suspension in hexanes and filtration. HRMS m/z calcd for C14H15N4OCl [M+H]+: 291.1007. Found: 291.1007.

Workup

  1. customThe product was isolated
  2. customafter silica gel purification with 20-40% EtOAc in hexanes gradient
  3. filtrationfiltration

Sources & evidence

ORD record
ord-d4ebcb040dd343938ff269a214625452
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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