Water → HCID 11371703, compound

HRID 897410Notes

Reaction equation

HRID 897410 reaction equation
[C-]#N.[Na+].O.[N:5]12CCN(CC1)C[CH2:6]2.[N:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[C:23](SC)[N:22]([CH3:27])[C:21](=[O:28])[C:20]=2[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)=[CH:15][CH:14]=1>CN1CCCC1=O>[CH3:27][N:22]1[C:21](=[O:28])[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)=[C:19]([C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)[N:24]=[C:23]1[C:6]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 9237DabcoHCID 9821070HCID 9821070, compound

Product 1

HCID 11371703HCID 11371703, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of NaCN (55 mg), water (0.1 ml) in 1-methyl-2-pyrrolidone (50 mL) was added 1,4-diazabicyclo[2,2,2]octane (220 mg, 2 mmole) and a solution of 365 mg of 6-(4-pyridyl)-3-methyl-2-methylthio-5-(3-(trifluoromethyl)phenyl)-(3H)-pyrimidin-4-one in 1-methyl-2-pyrrolidone (2 mL) at room temperature. The resulting mixture was stirred at room temperature for 5 minutes. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4 and then concentrated. The residue was purified by flash chromatography (20% EtOAc:Hexanes) to provide the product as a colorless oil; MS (m/z) 357 (M+H)+; C18H11F3N4O requir. 356.3.

Workup

  1. customat room temperature
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (20% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-fb6e1c21b3c747a59c82b164a3a30b65
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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