Tetrahydrofuran → 2-Chloro-5-(2,6-difluoro-4-pentylphenyl)pyrimidine

HRID 2209400Notes

Reaction equation

HRID 2209400 reaction equation
[CH2:1]([C:6]1[CH:11]=[C:10]([F:12])[C:9](B(O)O)=[C:8]([F:16])[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].Br[C:18]1[CH:19]=[N:20][C:21]([Cl:24])=[N:22][CH:23]=1.C1COCC1.O.O.O.O.O.O.O.O.O.O.B(O)([O-])[O-].B(O)(O)O.B(O)(O)O.B(O)(O)O.[Na+].[Na+]>O>[CH2:1]([C:6]1[CH:11]=[C:10]([F:12])[C:9]([C:18]2[CH:19]=[N:20][C:21]([Cl:24])=[N:22][CH:23]=2)=[C:8]([F:16])[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 6066655-Bromo-2-chloropyrimidineHCID 19380609HCID 19380609, compoundHCID 131719129HCID 131719129, compound

Product 1

HCID 193806082-Chloro-5-(2,6-difluoro-4-pentylphenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.22 mol of 4-pentyl-2,6-difluorophenylboronic acid (prepared from 5-pentyl-1,3-difluorobenzene and trimethyl borate using n-butyllithium), 0.18 mol of 5-bromo-2-chloropyrimidine, 550 ml of THF, 75 ml of an aqueous buffer solution (pH=8), 230 ml of an aqueous disodium tetraborate decahydrate solution (4%), 200 ml of water and 2 g of tetrakis[triphenylphosphine]palladium (0) is heated at the boil for 20 hours. Customary work-up gives the product, which can be further processed without purification.

Workup

  1. temperatureis heated at the boil for 20 hours
  2. customCustomary work-up gives the product, which
  3. customcan be further processed without purification

Sources & evidence

ORD record
ord-755107f75a8a470a8cdbaa32c81e6b70
Source dataset
uspto-grants-1995_10
Patent number
US05454975

Reaction notes

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