Acetonitrile → HCID 14988418, compound

HRID 2051503Notes

Reaction equation

HRID 2051503 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])=[N:6][CH:7]=1.[CH2:14](N(CC)CC)[CH3:15].C(#N)C.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[CH:14]([C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])=[N:6][CH:7]=1)=[CH2:15]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 14988417HCID 14988417, compound

Product 1

HCID 14988418HCID 14988418, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A glass-lined pressure vessel was charged with 4.85 g of 5-bromo-2-(isobutyramido)pyrimidine, 5.0 ml of triethylamine, 15 ml of acetonitrile, 245 mg of tris(O-tolyl)phosphine, and 55 mg of palladium acetate. The vessel was placed under an ethylene atmosphere at 200 psi and heated at 80° C. for 18 hours in a rocking autoclave. The vessel was cooled and then vented. The residue was treated with 50 ml of ether and the resulting mixture filtered. The solid was further washed with ether (2×25 ml). The organic filtrate was concentrated and then chromatographed on silica gel. Elution with methylene chloride:methanol (95:5) afforded 2.99 g of product, mp 110°-112° C.

Workup

  1. temperatureThe vessel was cooled
  2. filtrationthe resulting mixture filtered
  3. washThe solid was further washed with ether (2×25 ml)
  4. concentrationThe organic filtrate was concentrated
  5. customchromatographed on silica gel
  6. washElution with methylene chloride:methanol (95:5)

Sources & evidence

ORD record
ord-515233e9b9cd47ffb2c17064b5a19177
Source dataset
uspto-grants-1991_05
Patent number
US05019578

Reaction notes

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