Hydrochloric Acid → 2-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine

HRID 1728266Notes

Reaction equation

[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([O:22]CC)=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH3:3].[OH-].[Na+].C(O)COCCO.Cl>O>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([OH:22])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 7.5 g of 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-(ethoxy)pyrimidine, 10 g of sodium hydroxide and 120 ml of diethylene glycol was heated at 180° C. for 8 hours. The reaction mixture was poured into 100 ml of water, acidified with concentrated hydrochloric acid, then extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 100 ml of concentrated sodium chloride solution, dried over magnesium sulfate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 7:3) and recrystallization from ethyl alcohol gave 5.2 g of 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine.

Workup

extractionextracted three times with 50 ml of diethyl ether each time
washThe combined organic phases were washed twice with 100 ml of concentrated sodium chloride solution
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationsubsequently concentrated
customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 7:3) and recrystallization from ethyl alcohol

Sources & evidence

ORD record: ord-850956ee04af4ea7a73b175ab49c5bae
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326497

Reaction notes

Loading…