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

HRID 1728263
Notes
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Reaction equation

HRID 1728263 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 131814-Penten-1-OLHCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 190171162-(4-Bromophenyl)-5-ethoxypyrimidine

Product 1

HCID 540063702-[4-(5-Hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidineYield 80.1%

Reagents, catalysts & solvents 3

HCID 11776
Triphenylphosphine
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 962WaterSolvent

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

  1. extractionextracted three times with 50 ml of diethyl ether each time
  2. washThe combined organic phases were washed twice with 100 ml of concentrated sodium chloride solution each time
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationsubsequently concentrated
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes