Dimethylformamide → HCID 178504853, compound

HRID 750805Notes

Reaction equation

HRID 750805 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:7](S(C)(=O)=O)[N:6]=1)(=[O:4])=[O:3].[C-]#N.[K+].CN(C=[O:37])C>>[CH3:1][S:2]([C:5]1[N:6]=[C:7]([OH:37])[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:10]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 59753883HCID 59753883, compound

Product 1

HCID 178504853HCID 178504853, compound

Procedure

To a round bottom flask fitted with a magnetic stir bar and rubber septum was added 2 mL DMF, 6-[2,4-dichlorophenyl]-5-[4-chlorophenyl]-2,4-bis(methylsulfonyl)pyrimidine (Reference Example 5) (98 mg, 0.2 mmol) and potassium cyanide (15 mg, 0.22 mmol). The mixture was heated for 30 min at 80°. By LC, all starting material was consumed (Rt=3.59 min) and a new peak appeared (Rt=3.50 min). The molecular weight corresponded not to the cyano derivative, but to 2-methylsulfonyl-4-hydroxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine. (HPLC/MS: m/e=430 (M+)) probably due to the fact that the solvent was not anhydrous.

Workup

  1. customTo a round bottom flask fitted with a magnetic stir bar
  2. temperatureThe mixture was heated for 30 min at 80°
  3. customBy LC, all starting material was consumed (Rt=3.59 min)

Sources & evidence

ORD record
ord-fb27abce6a194038a88bd90b4ff02927
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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