Dimethylformamide → HCID 15953319, compound

HRID 271450Notes

Reaction equation

HRID 271450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][CH:15]([CH3:17])[CH3:16])[N:11]3[C:18](=[O:21])[NH:19][N:20]=[C:10]3[C:9]=2[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[CH3:29]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].CI>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][CH:15]([CH3:17])[CH3:16])[N:11]3[C:18](=[O:21])[N:19]([CH3:29])[N:20]=[C:10]3[C:9]=2[C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58772830HCID 58772830, compound

Product 1

HCID 15953319HCID 15953319, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of crude 7,8-bis(4-chlorophenyl)-5-(isopropylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one, DMF (0.7 mL), and potassium carbonate (21 mg, 0.15 mmol) was added methyl iodide (213 mg, 1.5 mmol). The resulting reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then diluted with EtOAc, washed with water and saturated aqueous NaCl, dried (Na2SO4), and concentrated at reduced pressure. The residue was purified by preparative reverse phase HPLC to obtain 14 mg (65% over two steps) of the title compound as a light yellow solid. HPLC/MS: retention time=4.54 min, [M+H]30 =428.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water and saturated aqueous NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-af07555976654c5aaa7291cf8e7e2d67
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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