Urea → HCID 65098712, compound

HRID 335000Notes

Reaction equation

HRID 335000 reaction equation
NC(N)=O.[I:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>N1C=CC=CC=1>[CH2:13]([NH:15][C:16]([NH:12][C:9]1[CH:8]=[CH:7][C:6]([I:5])=[CH:11][N:10]=1)=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 1176UreaHCID 8022Ethyl isocyanateHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 65098712HCID 65098712, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Step-1. 5-tributylstannanyl-pyridin-2-yl)-urea. (85) To 5-iodo-pyridin-2-ylamine (0.5 g, 2.27 mmol) in pyridine (2.5 mL) was added ethylisocyanate (0.24 g, 3.4 mmol)). The reaction mixture was stirred at room temperature for 72 h, concentrated. Water (40 mL) was added, stirred for 0.5 h, filtered, washed with water, dried to afford 0.61 g (92%) of 1-ethyl-3-(5-iodo-pyridin-2-yl)-urea, MR-66, as white solid. To MR-66 (0.5 g, 1.72 mmol) and bis-tributyltin (5.6 g, 9.64 mmol) in dioxane (25 mL) was added bis-triphenylphosphine palladium dichloride (0.28 g, 0.4 nmol). Ar gas was bubbled through the stirred reaction for 5 min. The reaction was stirred at 90° C. under Ar for 20 h. The reaction was cooled to room temperature, concentrated. The residue was purified by silica gel column chromatography using 30% ethyl acetate in hexanes to afford 0.41 g (53%) of (85) as viscous liquid.

Workup

  1. concentrationconcentrated
  2. additionWater (40 mL) was added
  3. stirringstirred for 0.5 h
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e53cf8d856444d089f531ebb0e565865
Source dataset
uspto-grants-2014_11
Patent number
US08883833B2

Reaction notes

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