Triethylamine → 2-chloro-N-cyclopropyl-5-fluoropyrimidin-4-amine

HRID 2400334Notes

Reaction equation

HRID 2400334 reaction equation
[Cl:1][C:2]1C=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.CC[N:12](CC)CC.[CH:17]1([NH2:20])[CH2:19][CH2:18]1>CC#N>[Cl:1][C:2]1[N:12]=[C:6]([NH:20][CH:17]2[CH2:19][CH2:18]2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 220610192,4-Dichloro-5-fluoropyridine

Product 1

HCID 53067942-chloro-N-cyclopropyl-5-fluoropyrimidin-4-amineYield 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To 2,4 dichloro-5-fluoropyridine (1 g, 6 mmol) dissolved in CH3CN (8 ml) cooled in an ice bath was added Et3N (1.16 ml, 8.4 mmol) and cyclopropylamine (0.29 ml, 8.4 mmol) in CH3CN (2 ml). Reaction stirred 0° C. for 2 hours, evaporated water added and reaction extracted with EtOAc (×3). The organic fractions were combined washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the product (0.92 g).

Workup

  1. temperaturecooled in an ice bath
  2. customReaction
  3. customevaporated water
  4. additionadded
  5. customreaction
  6. extractionextracted with EtOAc (×3)
  7. washThe organic fractions were combined washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e0cb507574b4ece835653e28df8ff43
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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