Water → HCID 18662980, compound

HRID 1956176Notes

Reaction equation

HRID 1956176 reaction equation
N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]([CH3:20])([CH3:19])[CH:8]2[C:11]2[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=2)=[CH:4][CH:3]=1.F[B-](F)(F)F.N#[O+].[C-:28]#[N:29].[K+].O>C(#N)C.CS(C)=O>[C:28]([C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]([CH3:19])([CH3:20])[CH:8]2[C:11]2[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=2)=[CH:4][CH:3]=1)#[N:29]

Participants

7

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 11137142Nitrilooxonium tetrafluoroborateHCID 18662979HCID 18662979, compound

Product 1

HCID 18662980HCID 18662980, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 1.0 g (3.5 mmol) of 5-(6-amino-2,2-dimethylindan-1-yl)-4-methylthiopyrimidine in 25 mL of dry acetonitrile was added with stirring 1.0 g (7.0 mmol) of nitrosonium tetrafluoroborate. The brown solution was allowed to react for 10 min and was then poured, with stirring, into a solution of 2.5 g (28 mmol) of cuprous cyanide and 3.0 g (47 mmol) of potassium cyanide in 150 mL of dry dimethyl sulfoxide. The resulting mixture was heated to 40° C. to form a solution and this solution was poured into 750 mL of water. The mixture obtained was extracted with ether (2×300 mL) and the ethereal extract was washed with water, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 500 mg (48 percent of theory) of the title compound as a light yellow solid melting at 157°-158° C.

Workup

  1. additionwas added
  2. customto react for 10 min
  3. additionwas then poured
  4. customto form a solution
  5. customThe mixture obtained
  6. extractionwas extracted with ether (2×300 mL)
  7. extractionthe ethereal extract
  8. washwas washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated by evaporation under reduced pressure
  12. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d0d0bff6f0b44c368cdc566d4b7acca7
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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