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

HRID 28566

반응식

HRID 28566 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1aa52f72aeb3402696cb72c3bb6ee3a3
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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