4-Bromobenzamide → HCID 19081571, compound

HRID 963379Notes

Reaction equation

HRID 963379 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([Sn](C)(C)C)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1.Br[C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH2:31])=[O:30])=[CH:27][CH:26]=1.[Cl-].[Li+]>O1CCOCC1>[C:29]([C:28]1[CH:32]=[CH:33][C:25]([C:16]2[C:17]([O:18][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([CH2:6][C:7]3[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=3)[CH:15]=2)=[CH:26][CH:27]=1)(=[O:30])[NH2:31]

Participants

5

Reactant 3

HCID 696834-BromobenzamideHCID 433294Lithium ChlorideHCID 19081555HCID 19081555, compound

Product 1

HCID 19081571HCID 19081571, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 g of 5-(3,4-dimethoxy-5-trimethylstannyl-benzyl)-pyrimidine-2,4-diamine (Example 1o) and 0.472 g of 4-bromobenzamide are dissolved in 50 ml of dioxan, treated with 0.3 g of lithium chloride and 0.15 g of tetrakis-triphenylphosphine-palladium and held at reflux under argon for 14 hrs. The mixture is poured on to ice-water, extracted with methylene chloride, dried over magnesium sulphate and, after concentration, the residue is chromatographed on silica gel with methylene chloride/methanol 2:1. 64 mg (7%) of 5-(4'-carbamoyl-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine are isolated as a colourless solid. M.p. 199° (decomposition).

Workup

  1. temperatureat reflux under argon for 14 hrs
  2. extractionextracted with methylene chloride
  3. dry with materialdried over magnesium sulphate
  4. concentrationafter concentration
  5. customthe residue is chromatographed on silica gel with methylene chloride/methanol 2:1

Sources & evidence

ORD record
ord-494ce565033c4cefbd6978ce0c40fbad
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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