Hydrogen Peroxide → N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-carbamoyl-4-pyridyl)-2-pyrimidineamine

HRID 976272Notes

Reaction equation

HRID 976272 reaction equation
OO.C=CCCCC.C(=O)([O-])[O-:10].[Na+].[Na+].[F:15][C:16]([F:42])([O:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]2[N:33]=[C:32]([C:34]3[CH:39]=[CH:38][N:37]=[C:36]([C:40]#[N:41])[CH:35]=3)[CH:31]=[CH:30][N:29]=2)[CH:24]=[CH:25][CH:26]=1)[CH:17]([F:19])[F:18]>CO>[F:42][C:16]([F:15])([O:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]2[N:33]=[C:32]([C:34]3[CH:39]=[CH:38][N:37]=[C:36]([C:40](=[O:10])[NH2:41])[CH:35]=3)[CH:31]=[CH:30][N:29]=2)[CH:24]=[CH:25][CH:26]=1)[CH:17]([F:19])[F:18]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 115971-HexeneHCID 19967016N-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamine

Product 1

HCID 19967025N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-carbamoyl-4-pyridyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.58 ml of hydrogen peroxide (30%), 0.16 ml of 1-hexene, 11 mg of sodium carbonate and 2 ml of methanol are added to 50 mg (0.12 mmol) of N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamine and the reaction mixture is stirred for 14 h at RT. The product is isolated by filtration, washed with methanol/water (9:1) and dried to give N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-carbamoyl-4-pyridyl)-2-pyrimidineamine; m.p. 224°-225°, FAB-MS: 408 (M+ +H), 290.

Workup

  1. customThe product is isolated by filtration
  2. washwashed with methanol/water (9:1)
  3. customdried

Sources & evidence

ORD record
ord-d4af68d52f1a4becb9135dbf4fb653da
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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