Sodium Carbonate → 5-Bromo2-(6-dodecyloxypyridin-3-yl)pyrimidine

HRID 376757Notes

Reaction equation

HRID 376757 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][N:23]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.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>[Br:8][C:5]1[CH:4]=[N:3][C:2]([C:25]2[CH:24]=[N:23][C:22]([O:21][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:27][CH:26]=2)=[N:7][CH:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 109555882,5-DibromopyrimidineHCID 224128212-Dodecyloxypyridine-5-boronic acid

Product 1

HCID 178694045-Bromo2-(6-dodecyloxypyridin-3-yl)pyrimidineYield 35%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A reaction of 35 mmol of 2,5-dibromopyrimidine, 27 mmol of 2-dodecyloxypyridine-5-boronic acid, 64 mmol of sodium carbonate and 0.3 mmol of tetrakis(triphenylphosphine)palladium(0) in 210 ml of toluene, 135 ml of ethanol and 70 ml of water is carried out analogously to the procedure indicated for precursor 3. Corresponding purification gives 3.9 g (35%) of a colorless solid.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-56f0ed06153c45a2a23023a3db7214b7
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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