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

HRID 376755Notes

Reaction equation

HRID 376755 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][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 193590955-Bromo-2-(6-butoxypyridin-3-yl)pyrimidineYield 37%

Reagents, catalysts & solvents 4

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

Procedure

A reaction of 109 mmol of 2,5-dibromopyrimidine, 109 mmol of 2-butoxypyridine-5-boronic acid, 218 mmol of sodium carbonate and 1.1 mmol of tetrakis(triphenylphosphine)palladium(0) in 200 ml of toluene, 100 ml of ethanol and 100 ml of water is carried out analogously to the procedure indicated for precursor 3. Corresponding purification gives 12.4 g (37%) of a colorless solid, m.p. 134-138° C.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-80fe51dc663c41058304c82908047d68
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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