Sodium Carbonate → 2-Amino-4-chloro-6-(5-chloro-2-methoxyphenyl)-5-methyl-pyrimidine

HRID 28566

Reaction equation

HRID 28566 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[C:4]([Cl:10])[N:3]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16](B(O)O)[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[NH2:1][C:2]1[N:3]=[C:4]([Cl:10])[C:5]([CH3:9])=[C:6]([C:14]2[CH:13]=[C:12]([Cl:11])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[N:7]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2467512-Amino-4,6-dichloro-5-methylpyrimidineHCID 27357515-Chloro-2-methoxyphenylboronic acid

Product 1

HCID 860043262-Amino-4-chloro-6-(5-chloro-2-methoxyphenyl)-5-methyl-pyrimidineYield 21.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 2-amino-4,6-dichloro-5-methyl-pyrimidine (0.18 g, 1.0 mmol), 5-chloro-2-methoxy-phenyl boronic acid (0.19 g, 1.0 mmol), palladium (II) acetate (0.034 g, 0.15 mmol) and triphenylphosphine (0.079 g, 0.30 mmol) was added a solution of sodium carbonate (0.64 g, 6.0 mmol) in water (5 ml) followed by glyme (20 ml). The mixture was stirred under an argon atmosphere at room temperature for 72 hours. Filtration and concentration of the filtrate yielded a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide 2-amino-4-chloro-6-(5-chloro-2-methoxyphenyl)-5-methyl-pyrimidine (0.06 g, 21% yield) as a white powder.

Workup

  1. filtrationFiltration and concentration of the filtrate
  2. customyielded a residue which
  3. customwas purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-1aa52f72aeb3402696cb72c3bb6ee3a3
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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