Methylhydrazine → HCID 58266267, compound

HRID 2039701Notes

Reaction equation

HRID 2039701 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17]CC)=O)=[C:13]([CH2:20]Br)[N:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:23]=3)[C:11](=[O:33])[NH:10]2)=[CH:5][CH:4]=1)#[N:2].[CH3:34][NH:35][NH2:36]>O1CCOCC1>[F:28][C:25]1[CH:26]=[CH:27][C:22]([N:12]2[C:13]3[CH2:20][N:35]([CH3:34])[NH:36][C:15](=[O:17])[C:14]=3[CH:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[NH:10][C:11]2=[O:33])=[CH:23][C:24]=1[C:29]([F:32])([F:31])[F:30]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 58266282HCID 58266282, compound

Product 1

HCID 58266267HCID 58266267, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

527 mg (1.0 mmol) of ethyl 4-(4-cyanophenyl)-1-[4-fluoro-3-(trifluoromethyl)phenyl]-6-(bromomethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate were dissolved in 25 ml of dioxane, and 138 mg (3.0 mmol; 3 eq.) of methylhydrazine were added. The mixture was stirred at 120° C. for 1 h and then concentrated. The residue was purified directly by preparative HPLC (column: Gromsil C-18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). This gave 270 mg (55% of theory) of the target compound.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified directly by preparative HPLC (column: Gromsil C-18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)

Sources & evidence

ORD record
ord-f384ace35a394900868b4121391e9a07
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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