tert-Butyl hydroperoxide → HCID 87081215, compound

HRID 1046836Notes

Reaction equation

HRID 1046836 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:11](=S)[NH:10]2)=[CH:5][CH:4]=1)#[N:2].C([O:33]O)(C)(C)C.[OH2:35].[NH2:36][NH2:37]>C(O)C.C1(C)C=CC=CC=1>[F:25][C:24]([F:27])([F:26])[C:20]([OH:33])=[O:35].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:11]([NH:36][NH2:37])=[N:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 6410tert-Butyl hydroperoxide2×HCID 24654Hydrazine hydrate (1:1)2×HCID 87081182HCID 87081182, compound

Product 1

HCID 87081215HCID 87081215, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

4-(4-Cyanophenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (100 mg, 0.25 mmol) was dissolved in a mixture of ethanol (10 ml) and toluene (5 ml). At 0° C., tert-butyl hydroperoxide (3 M solution in toluene, 602 μl, 1.81 mmol, 7.2 eq.) was added dropwise. The mixture was stirred at RT for 3 h, and hydrazine hydrate (183 μl, 3.76 mmol, 15 eq.) was then added. After 12 h of stirring, more tert-butyl hydroperoxide solution (3 M in toluene, 167 μl, 0.50 mmol, 2 eq.) and hydrazine hydrate (49 μl, 1.00 mmol, 4 eq.) were added, and the mixture was stirred for a further 3 h. The mixture was then substantially concentrated under reduced pressure, water (2 ml) was added and the remaining organic solvents were distilled off. The aqueous residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the title compound was obtained as a solid (13.7 mg, 14% of theory).

Workup

  1. stirringAfter 12 h of stirring
  2. stirringthe mixture was stirred for a further 3 h
  3. concentrationThe mixture was then substantially concentrated under reduced pressure, water (2 ml)
  4. additionwas added
  5. distillationthe remaining organic solvents were distilled off
  6. customThe aqueous residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)

Sources & evidence

ORD record
ord-b509c4903daf4a1b8aa0f57bb5a3bc6e
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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