4-Penten-1-OL → 2-[4-(5-Hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidine

HRID 1728263Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:17]([OH:22])[CH2:18][CH2:19][CH:20]=[CH2:21].C(=O)(O)[O-].[Na+].CN1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[OH:22][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 14.7 g of 2-(4-bromophenyl)-5-(ethoxy)-pyrimidine, 5.7 g of 4-penten-1-ol, 10 g of sodium bicarbonate and 20 ml of N-methylpyrrolidone was treated with 0.3 g of triphenylphosphine and 0.12 g of palladium acetate. The reaction mixture was heated at 120° C. for 2 hours under a nitrogen atmosphere, then poured into 100 ml of water and 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 each time, dried over magnesium sulfate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol gave 12 g of 2-[4-(5-hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidine.

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 each time
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationsubsequently concentrated
customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol

Sources & evidence

ORD record: ord-d4da905fb90343e6a579231fa0f5ca90
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326497

Reaction notes

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