N-Ethylbenzylamine → HCID 22599759, compound

HRID 1592191Notes

Reaction equation

HRID 1592191 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][CH3:12])[N:5]=[CH:4][N:3]=1.[CH2:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:14]>C(O)C>[CH2:9]([O:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:15]([CH2:13][CH3:14])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1)[C:10]#[C:11][CH3:12]

Participants

4

Reactant 2

HCID 84352N-EthylbenzylamineHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599759HCID 22599759, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4 ml of ethanol were added 0.5 g of 4-chloro-6-(2-butynyloxy)pyrimidine and 0.68 g of N-ethyl-N-benzylamine, followed by heating under reflux for 6 hours. The reaction mixture was then left for cooling to room temperature and concentrated under reduced pressure. A saturated aqueous ammonium chloride solution was poured onto the residue, which was extracted three times with ethyl acetate. The organic layers were combined and washed with a saturated aqueous sodium chloride solution, and the combined organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.42 g of 6-(2-butynyloxy)-4-(N-ethyl-N-benzylamino)pyrimidine (the present compound (129)).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. waitThe reaction mixture was then left
  4. concentrationconcentrated under reduced pressure
  5. additionA saturated aqueous ammonium chloride solution was poured onto the residue, which
  6. extractionwas extracted three times with ethyl acetate
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-250321fb4aa24509914b8eec16a601b6
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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