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

HRID 28566

反応式

HRID 28566 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1aa52f72aeb3402696cb72c3bb6ee3a3
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

関連ノート

読み込み中…