Sodium Carbonate → 2-(2,3-Difluoro-4-octylphenyl)-5-(6-hexyloxypyridin-3-yl)pyrimidine

HRID 376778Notes

Reaction equation

HRID 376778 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[F:21][C:22]1[C:27]([F:28])=[C:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:25]=[CH:24][C:23]=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>[F:21][C:22]1[C:27]([F:28])=[C:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:25]=[CH:24][C:23]=1[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=2)=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 19359093(2,3-Difluoro-4-octylphenyl)boronic acidHCID 193591062-Chloro-5-(6-hexyloxypyridin-3-yl)pyrimidine

Product 1

HCID 193591152-(2,3-Difluoro-4-octylphenyl)-5-(6-hexyloxypyridin-3-yl)pyrimidineYield 39%

Reagents, catalysts & solvents 4

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

Procedure

The reaction of 2.5 mmol of 2-chloro-5-(6-hexyloxypyridin-3-yl)pyrimidine, 2.5 mmol of 2,3-difluoro-4-octylphenylboronic acid, 5 mmol of sodium carbonate and 0.025 mmol of tetrakis(triphenylphosphine)palladium(0) in 8 ml of toluene, 4 ml of ethanol and 4 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 dichloromethane/ethyl acetate 98:2 (v/v) as eluent and is recrystallized from acetonitrile, giving 0.47 g (39%) of colorless crystals, X 94.5 SC 125.5 SA 156 I.

Workup

  1. customThe crude product is separated off by column chromatography on silica gel 60 using dichloromethane/ethyl acetate 98:2 (v/v) as eluent
  2. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5e29e5bbd6d04f9e99cabb59465b956b
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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