Sodium Carbonate → 5-Bromo-2-(6-octyloxypyridin-3-yl)pyrimidine

HRID 376756Notes

Reaction equation

HRID 376756 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][N:15]=1)[CH2:10][CH2:11][CH3:12].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:17]2[CH:16]=[N:15][C:14]([O:13][CH2:9][CH2:10][CH2:11][CH2:12][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:19][CH:18]=2)=[N:7][CH:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 109555882,5-DibromopyrimidineHCID 45116227(6-Butoxypyridin-3-yl)boronic acid

Product 1

HCID 193590915-Bromo-2-(6-octyloxypyridin-3-yl)pyrimidineYield 75.9%

Reagents, catalysts & solvents 4

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

Procedure

A reaction of 115 mmol of 2,5-dibromopyrimidine, 115 mmol of 2-butoxypyrdine-5-boronic acid, 230 mmol of sodium carbonate and 1.2 mmol of tetrakis(triphenylphosphine)palladium(0) in 280 ml of toluene, 140 ml of ethanol and 140 ml of water is carried out analogously to the procedure indicated for precursor 3. Corresponding purification gives 15.9 g (38%) of a colorless solid, m.p. 99-101 ° C.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-443f576be76647e889e72cdc00ae6c8e
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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