1-Bromopropane → 2-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-(ethoxy)pyrimidine

HRID 1728265Notes

Reaction equation

HRID 1728265 reaction equation
[H-].[Na+].O1C[CH2:6][CH2:5][CH2:4]1.[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][N:21]=2)=[CH:16][CH:15]=1.C(Br)CC>O>[CH2:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][N:21]=2)=[CH:18][CH:19]=1)[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 190170732-[4-(5-Hydroxy-1-pentyl)phenyl]-5-(ethoxy)pyrimidine

Product 1

HCID 190171772-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-(ethoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.2 g of sodium hydride (60-65 wt. %) and 150 ml of tetrahydrofuran was treated with 8.5 g of 2-[4-(5-hydroxy-1-pentyl)phenyl]-5-(ethoxy)pyrimidine while gassing with nitrogen, stirred for 5 hours, treated with 4 g of propyl bromide and subsequently stirred at room temperature overnight. The reaction mixture was treated with 500 ml of water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time, dried over magnesium sulfate, filtered and subsequently concentrated. Chromato- graphy of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) and recrystallization from ethyl alcohol gave 7.5 g of pure 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-(ethoxy)pyrimidine.

Workup

  1. stirringsubsequently stirred at room temperature overnight
  2. extractionextracted three times with 50 ml of diethyl ether each time
  3. washThe combined organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationsubsequently concentrated
  7. customChromato- graphy of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) and recrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-5480922e53ce4baebfe4b8400c556fa3
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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