Sodium Carbonate → 5-(6-Butoxypyridin-3-yl)-2-chloropyrimidine

HRID 376759Notes

Reaction equation

HRID 376759 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=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>[CH2:9]([O:13][C:14]1[N:15]=[CH:16][C:17]([C:2]2[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=2)=[CH:18][CH:19]=1)[CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 45116227(6-Butoxypyridin-3-yl)boronic acid

Product 1

HCID 193591035-(6-Butoxypyridin-3-yl)-2-chloropyrimidineYield 38%

Reagents, catalysts & solvents 4

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

Procedure

A reaction of 109 mmol of 5-bromo-2-chloropyrimidine, 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 10.8 g (38%) of a colorless solid, m.p. 117° C., cl.p. 130° C.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-6f8df8f3641d4a9d8f51d3cac7b0a08c
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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