Phosphorus oxychloride → HCID 86619138, compound

HRID 2238648Notes

Reaction equation

HRID 2238648 reaction equation
O=[C:2]1[NH:7][C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])=[N:5][CH:4]=[C:3]1[C:17]#[N:18].P(Cl)(Cl)([Cl:21])=O>C(#N)C>[Cl:21][C:2]1[C:3]([C:17]#[N:18])=[CH:4][N:5]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68686378HCID 68686378, compound

Product 1

HCID 86619138HCID 86619138, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

1.69 g of the 6-oxo-2-{[(1S)-1-phenylethyl]amino}-1,6-dihydro-5-pyrimidinecarbonitrile [54-1] was dissolved in 100 mL of acetonitrile, then 5 mL of phosphorus oxychloride was added, and stirred at 85° C. for 2 hours. After concentrating the reaction mixture under reduced pressure, the obtained residue was placed in an ice bath, extracted with ethyl acetate, and the organic layer was washed with water and saturated brine in the subsequent order. After drying over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and 1.54 g of 4-chloro-2-{[(1S)-1-phenylethyl]amino}-5-pyrimidinecarbonitrile [54-2] was obtained as an oily product.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure
  2. customthe obtained residue was placed in an ice bath
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine in the subsequent order
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. filtrationthe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a5b1b102d0454944831170b2b784c253
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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