Methylhydrazine → HCID 44480524, compound

HRID 2039694Notes

Reaction equation

HRID 2039694 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][C@H:5]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)[C:4]=1[C:28](OCC)=[O:29].[CH3:33][NH:34][NH2:35]>O1CCOCC1>[CH3:33][N:34]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][C@H:5]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[C:4]=2[C:28](=[O:29])[NH:35]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 58266264HCID 58266264, compound

Product 1

HCID 44480524HCID 44480524, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

101 g (198.7 mmol) of ethyl (4R)-6-(bromomethyl)-4-(4-cyanophenyl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate (Example 6A) were initially charged in 2400 ml of dioxane. 27.46 g (596.1 mmol) of methylhydrazine were added dropwise to the solution, and the reaction mixture was then stirred at boiling point for 3 h. The mixture was then concentrated, and the residue was dissolved in dichloromethane and washed with water. The organic phase was dried over sodium sulphate and concentrated. The residue that remained was chomatographed on silica gel (mobile phase: dichloromethane/methanol 95:5). The solid which was obtained after concentration of the product fractions was triturated with diethyl ether, filtered off with suction and then dried at 50° C. under reduced pressure for 4 days. This gave 56.8 g (66% of theory) of the title compound.

Workup

  1. customfor 3 h
  2. concentrationThe mixture was then concentrated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe solid which was obtained after concentration of the product fractions
  8. customwas triturated with diethyl ether
  9. filtrationfiltered off with suction
  10. customdried at 50° C. under reduced pressure for 4 days

Sources & evidence

ORD record
ord-dcf101a27c524eff9e97b7e26b5e100d
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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