Potassium Phosphate, Tribasic → 6-(5-Chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28547

Reaction equation

HRID 28547 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:5]=[C:4]([NH2:16])[CH:3]=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:27][CH3:28])=[C:22](B(O)O)[CH:23]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:27][CH3:28])=[C:20]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=3)[N:5]=[C:4]([NH2:16])[CH:3]=2)[CH:19]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 860043166-Chloro-N2-(4-chlorophenyl)pyrimidine-2,4-diamine

Product 1

HCID 114852166-(5-Chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamineYield 30%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 6-chloro-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine (0.077 g, 0.30 mmol), 5-chloro-2-methoxy-phenyl boronic acid (0.112 g, 0.60 mmol), palladium (II) acetate (0.017 g, 0.075 mmol), 2-(dicyclohexylphosphino)biphenyl (0.105 g, 0.30 mmol) and potassium phosphate (0.254 g, 1.2 mmol) in dry toluene (3.5 ml) was heated at 90-100° C. under an argon atmosphere for 18 hours. After cooling to room temperature, ether (20 ml) was added and the mixture was washed with aqueous sodium hydroxide solution (1.0 M, 10 ml), with saturated aqueous sodium chloride solution (10 ml), and dried over magnesium sulfate. After concentrating under reduced pressure, the residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide the title compound (0.032 g, 30% yield) as a white powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with aqueous sodium hydroxide solution (1.0 M, 10 ml), with saturated aqueous sodium chloride solution (10 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentrating under reduced pressure
  5. customthe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-2a8f2e02149a486185b496f807fc8ddf
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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