Methylhydrazine → HCID 44480784, compound

HRID 2039696Notes

Reaction equation

HRID 2039696 reaction equation
Br[CH2:2][C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7](=[O:19])[NH:6][CH:5]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=2[C:28]([F:31])([F:30])[F:29])[C:4]=1[C:32]([O:34]CC)=O.[CH3:37][NH:38][NH2:39]>O1CCOCC1>[CH3:37][N:38]1[CH2:2][C:3]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:16])[F:18])[CH:10]=3)[C:7](=[O:19])[NH:6][CH:5]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=3[C:28]([F:29])([F:31])[F:30])[C:4]=2[C:32](=[O:34])[NH:39]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 58266257HCID 58266257, compound

Product 1

HCID 44480784HCID 44480784, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under an atmosphere of argon protective gas, ethyl 6-(bromomethyl)-4-[4-cyano-2-(trifluoro-methyl)phenyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate (576 mg, 1 mmol; Example 21A) was initially charged in dioxane (20 ml). Methylhydrazine (128 mg, 3 mmol) was added dropwise to the reaction mixture, and the mixture was then stirred at boiling point for 8 h (bath temperature 120° C.). The reaction mixture was then concentrated, and the residue was purified by preparative HPLC (column: Gromsil C18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). This gave the target compound as a solid which was reprecipitated from acetonitrile/water (Yield: 205 mg, 41% of theory).

Workup

  1. customfor 8 h
  2. custom(bath temperature 120° C.)
  3. concentrationThe reaction mixture was then concentrated
  4. customthe residue was purified by preparative HPLC (column: Gromsil C18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)

Sources & evidence

ORD record
ord-2f6ad1fc0ffd4ed59211138e7ac37def
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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