Sodium Hydroxide → (-)-5-Decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine

HRID 1956084Notes

Reaction equation

HRID 1956084 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].[OH:27][CH:28]([CH3:34])[CH2:29][CH2:30][CH2:31][C:32]#[CH:33].[B]1OC2C(=CC=CC=2)O1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH:33]=[CH:32][CH2:31][CH2:30][CH2:29][CH:28]([OH:27])[CH3:34])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 6327445BenzcatechinboraneHCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 133371736-Heptyn-2-ol

Product 1

HCID 53726462(-)-5-Decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a reactor equipped with a stirrer and a thermometer, 5-decyloxy-2-(4-bromophenyl)pyrimidine (13.98 g), dry tetrahydrofuran (THF) (30 ml), tetrakis(triphenylphosphine)palladium (0.11 g) and sodium hydroxide (1.2 g) are charged. To the mixture, a solution of a reaction product of 6-hydroxy-1-heptyne and catechol borane (5 g) dissolved in THF (12 ml) is dropwise added, followed by heating up to a refluxing temperatur. After reacting for 4 hours, the reaction mixture is cooled to room temperature. To the mixture, toluene and water are added for extraction, and the organic layer is washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine (7.99 g).

Workup

  1. customIn a reactor equipped with a stirrer
  2. additionis dropwise added
  3. temperatureby heating up to a refluxing temperatur
  4. washthe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customA resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

Sources & evidence

ORD record
ord-8a8ce80cea944b04bf606a5037419e41
Source dataset
uspto-grants-1998_07
Patent number
US05779934

Reaction notes

Loading…