Hydrogen Peroxide → N-(3-chloro-phenyl)-4-(2-carbamoyl-4-pyridyl)-2-pyrimidineamine

HRID 724823Notes

Reaction equation

HRID 724823 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([C:21]#[N:22])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.OO.C=CCCCC.C(=O)([O-])[O-:32].[Na+].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([C:21](=[O:32])[NH2:22])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 115971-HexeneHCID 196896104-{2-[(3-Chlorophenyl)amino]pyrimidin-4-yl}pyridine-2-carbonitrile

Product 1

HCID 19711151N-(3-chloro-phenyl)-4-(2-carbamoyl-4-pyridyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 mg (0.16 mmol) of N-(3-chloro-phenyl)-4-(2-cyano-4-pyridyl)-2-pyrimidineamine are suspended in 2 ml of methanol. 0.58 ml of hydrogen peroxide (30% strength), 0.16 ml of 1-hexene and 11 mg of sodium carbonate are added and the reaction mixture is stirred for 14 hours at RT. The product is isolated by filtration, washed (methanol:water=1:1) and dried at 50° under HV. N-(3-chloro-phenyl)-4-(2-carbamoyl-4-pyridyl)-2-pyrimidineamine is obtained in the form of a yellow powder; m.p. 245°-247°, Rf =0.23 (n-hexane:ethyl acetate=1:1).

Workup

  1. customThe product is isolated by filtration
  2. washwashed (methanol:water=1:1)
  3. customdried at 50° under HV

Sources & evidence

ORD record
ord-5385654413ed4614b78d807c251a48bf
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Reaction notes

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