Sodium Carbonate → 6-(5-Chloro-2-methoxy-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamine

HRID 28528

反応式

HRID 28528 の反応式
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[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(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>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:27][CH3:28])=[C:20]([C:2]2[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[CH:3]=2)[CH:19]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2387486-Chloro-n4-(4-methylphenyl)pyrimidine-2,4-diamineHCID 27357515-Chloro-2-methoxyphenylboronic acid

生成物 1

HCID 113138316-(5-Chloro-2-methoxy-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamine収率 86%

試薬・触媒・溶媒 3

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

反応条件

温度
92.5 °C

実験手順

To a mixture of 6-chloro-N*4*-p-tolyl-pyrimidine-2,4-diamine (2.8 g, 11.9 mmol), 5-chloro-2-methoxy-phenyl boronic acid (3.96 g, 21.5 mmol), palladium (II) acetate (0.2 g, 0.9 mmol) and triphenylphosphine (0.47 g, 1.8 mmol) was added a solution of sodium carbonate (6.36 g, 60 mmol) in water (20 ml) followed by glyme (100 ml). The mixture was stirred under an argon atmosphere at 90-95° C. for 18 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 the title compound (3.48 g, 86% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.27 (s, 3H, CH3), 3.88 (s, 3H, CH3), 6.27 (s, 2H, NH2), 6.72 (s, 1H, Ar), 7.10 (d, 2H, J=8.3 Hz, Ar), 7.16 (d, 1H, J=8.9 Hz, Ar), 7.44 (dd, 1H, J=8.9 Hz, J=2.8 Hz, Ar), 7.63 (d, 2H, J-8.3 Hz, Ar), 7.92 (d, 1H, J=2.8 Hz, Ar), 9.10 (s, 1H, NH).

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-686c3494ee2b4f5ab7659115bd34192e
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

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