1-Propanamine, N-ethyl- → HCID 69432697, compound

HRID 1592231Notes

Reaction equation

HRID 1592231 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10](Cl)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH2:14]([NH:16][CH2:17][CH2:18][CH3:19])[CH3:15]>C(O)C>[CH2:1]([O:5][C:6]1[N:7]=[CH:8][N:9]=[C:10]([N:16]([CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15])[C:11]=1[F:12])[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 883981-Propanamine, N-ethyl-HCID 225997174-(2-Butynyloxy)-5-fluoro-6-chloropyrimidine

Product 1

HCID 69432697HCID 69432697, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.5 ml of ethanol ware added 0.1 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine and 0.11 g of N-ethylpropylamine, followed by heating under reflux for 10 hours. The reaction mixture was then left for cooling to room temperature and concentrated under reduced pressure. The residue was added water and extracted three times with t-butyl methyl ether. The organic layers were combined, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.15 g of 6-(2-butynyloxy)-4-(N-ethylpropylamino)-5-fluoropyrimidine (the present compound (185)).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 10 hours
  3. waitThe reaction mixture was then left
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was added water
  6. extractionextracted three times with t-butyl methyl ether
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4c2d47948be34e229ef5408f9d556992
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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