Propylamine → 4,6-Di(2-furyl)-5-[2-(propylamino)-4-pyridyl]-2-pyrimidinamine

HRID 747165Notes

Reaction equation

HRID 747165 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)=[N:10][C:11]([NH2:19])=[N:12][C:13]=2[C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=1.[CH2:25]([NH2:28])[CH2:26][CH3:27]>>[O:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[C:9]1[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:28][CH2:25][CH2:26][CH3:27])[CH:7]=2)=[C:13]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[N:12]=[C:11]([NH2:19])[N:10]=1

Participants

3

Reactant 2

HCID 7852PropylamineHCID 23020419HCID 23020419, compound

Product 1

HCID 597490934,6-Di(2-furyl)-5-[2-(propylamino)-4-pyridyl]-2-pyrimidinamineYield 64%

Conditions

Temperature
120 °C

Procedure

In a reaction vessel, 5-(2-fluoro-4-pyridyl)-4,6-di(2-furyl)-2-pyrimidinamine (200 mg, 0.621 mmol) and n-propylamine (5 ml) were mixed together and the mixture was stirred at 120° C. After 18 hours, the reaction mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over anhydrous sodium sulfate and then the filtrate was concentrated. The resulting solid was suspended in ethanol, collected by filtration and washed with ethanol, to give the title compound (64%,72 mg) as a pale yellow solid.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationthe filtrate was concentrated
  5. filtrationcollected by filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-cb2fec0bde784a8fb04f504fae7bee61
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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