Potassium Cyanide → HCID 86608508, compound

HRID 1678079Notes

Reaction equation

HRID 1678079 reaction equation
[C-]#N.[K+].C([O-])(O)=O.[Na+].[C:9]([C:13]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[CH:34]=[C:33]([CH3:35])[C:32]([SH:36])=[N:31][C:30]3=[O:37])[CH2:21][CH2:20]2)[CH:16]=[C:15]([C:38]([F:41])([F:40])[F:39])[N:14]=1)([CH3:12])([CH3:11])[CH3:10].C1OCCOCCOCCOCCOCCOC1.Br[C:61]#[N:62]>C(Cl)Cl>[C:9]([C:13]1[N:18]=[C:17]([N:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[CH:34]=[C:33]([CH3:35])[C:32]([S:36][C:61]#[N:62])=[N:31][C:30]3=[O:37])[CH2:23][CH2:24]2)[CH:16]=[C:15]([C:38]([F:40])([F:41])[F:39])[N:14]=1)([CH3:10])([CH3:11])[CH3:12]

Participants

7

Reactant 5

HCID 9032Potassium CyanideHCID 10476Cyanogen BromideHCID 2855718-Crown-6HCID 516892Sodium BicarbonateHCID 178430501HCID 178430501, compound

Product 1

HCID 86608508HCID 86608508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of KCN (325.6 mg, 5.0 mmol) in 5% strength NaHCO3 solution (7 ml) was added to 484.6 mg (1.0 mmol) of 1-(4-{4-[2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}butyl)-4-mercapto-5-methylpyrimidin-2(1H)-one from Example 2 in 20 ml of methylene chloride. Then a mixture of 2.0 mg of 18-crown-6 and 105.9 mg (1.0 mmol) of BrCN, in the minimum amount of methylene chloride necessary to dissolve, was added dropwise at 0° C. The organic phase was then separated off and washed twice with saturated aqueous brine. The organic phase was dried over Na2SO4 and filtered to remove the desiccant, and the solvent was evaporated to dryness in vacuo; yield: 420.0 mg. 1-(4-{4-[2-tert-Butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}butyl)-5-methyl-2-oxo-1,2-dihydropyrimidin-4-yl thiocyanate was employed without additional purification in the next step.

Workup

  1. additionwas added dropwise at 0° C
  2. customThe organic phase was then separated off
  3. washwashed twice with saturated aqueous brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customto remove the desiccant, and the solvent
  7. customwas evaporated to dryness in vacuo
  8. custom1-(4-{4-[2-tert-Butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}butyl)-5-methyl-2-oxo-1,2-dihydropyrimidin-4-yl thiocyanate was employed without additional purification in the next step

Sources & evidence

ORD record
ord-80631159f2294adc92a06fe4cdb0d105
Source dataset
uspto-grants-2011_08
Patent number
US08008488B2

Reaction notes

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