Sodium Carbonate → 5-(6-Butoxypyridin-3-yl)-2-(2,3-difluoro-4-octylphenyl)pyrimidine

HRID 376779Notes

Reaction equation

HRID 376779 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[N:14][C:15](Cl)=[N:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[F:19][C:20]1[C:25]([F:26])=[C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:23]=[CH:22][C:21]=1B(O)O.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>[CH2:1]([O:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[N:14][C:15]([C:21]3[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:25]([F:26])[C:20]=3[F:19])=[N:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 19359093(2,3-Difluoro-4-octylphenyl)boronic acidHCID 193591035-(6-Butoxypyridin-3-yl)-2-chloropyrimidine

Product 1

HCID 193590995-(6-Butoxypyridin-3-yl)-2-(2,3-difluoro-4-octylphenyl)pyrimidineYield 46.3%

Reagents, catalysts & solvents 4

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

Procedure

The reaction of 2 mmol of 5-(6-butoxypyridin-3-yl)-2-chloropyrimidine, 2.2 mmol of 2,3-difluoro-4-octylphenylboronic acid, 4 mmol of sodium carbonate and 0.02 mmol of tetrakis(triphenylphosphine)palladium(0) in 10 ml of toluene, 5 ml of ethanol and 5 ml of water is carried out analogously to the procedure indicated for Example 1a). The crude product is separated off by column chromatography on silica gel 60 using heptane/ethyl acetate 9:1 (v/v) as eluent and is recrystallized from acetonitrile, giving 0.42 g (46%) of colorless crystals, X 84 SC 73 SA 162 I.

Workup

  1. customThe crude product is separated off by column chromatography on silica gel 60 using heptane/ethyl acetate 9:1 (v/v) as eluent
  2. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-9b85a02714b14e8e949e1180d270338f
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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