Hydrogen Peroxide → HCID 11567488, compound

HRID 2223138Notes

Reaction equation

HRID 2223138 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[F:16])=[C:6]([NH:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])[N:5]=[C:4]([C:24]#[N:25])[N:3]=1.C([O-])([O-])=[O:27].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[C:7]([C:8]2[C:9]([F:16])=[CH:10][C:11]([F:15])=[CH:12][C:13]=2[F:14])=[C:6]([NH:17][C@@H:18]([CH3:23])[C:19]([F:20])([F:21])[F:22])[N:5]=[C:4]([C:24]([NH2:25])=[O:27])[N:3]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 11689444HCID 11689444, compound

Product 1

HCID 11567488HCID 11567488, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
10 °C

Procedure

5.0 g of 4-chloro-6-((S)-2,2,2-trifluoro-1-methylethylamino)-5-(2,4,6-trifluorophenyl)-pyrimidine-2-carbonitrile (see WO 03/04993, pages 28 and 29) were initially charged in 5 ml of DMSO, 344 mg of K2CO3 were added and the mixture was cooled to 10° C. 1.4 ml of 30% strength H2O2 were then added. The mixture was stirred in an ice bath for 5 min and then at room temperature for another 30 min. The reaction mixture was introduced into 150 ml of water. During the addition, the amide precipitated out. The amide was filtered off, washed and dried under high vacuum. This gave 4.7 g of the beige title compound of m.p. 157-162° C.

Workup

  1. waitat room temperature for another 30 min
  2. additionDuring the addition
  3. customthe amide precipitated out
  4. filtrationThe amide was filtered off
  5. washwashed
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-57d4742be0344802b103de6655d1ae2b
Source dataset
uspto-grants-2008_05
Patent number
US07375108B2

Reaction notes

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