Potassium Carbonate → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(3-chlorophenyl)pyrimidine-2,4-diamine

HRID 2386987ノート

反応式

HRID 2386987 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(Cl)Cl.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:20])[CH:26]=3)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2734323(3-Chlorophenyl)boronic acidHCID 71681979N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-chloropyrimidine-2,4-diamine

生成物 1

HCID 44595856N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(3-chlorophenyl)pyrimidine-2,4-diamine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

The product of Example 6A (69 mg, 0.246 mmol), 3-chlorophenylboronic acid (42 mg, 0.270 mmol), dichlorobis((triphenylphosphine)palladium(II) (17 mg, 0.025 mmol), and potassium carbonate (100 mg, 0.724 mmol) were combined with dioxane (5 mL) and water (1.5 mL) and heated to 100° C. overnight. The mixture was diluted with methylene chloride, washed with water, and absorbed on silica gel and purified using silica gel chromatography, eluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.98 (s, 1H) 7.76-7.86 (m, 1H) 7.61 (d, J=5.76 Hz, 1H) 7.41-7.52 (m, 2H) 7.00 (s, 1H) 6.86 (s, 1H) 6.28 (s, 1H) 6.08 (s, 2H) 5.85 (s, 2H) 5.69-5.77 (m, 1H) 3.33-3.50 (m, 4H); MS (ESI+) m/z 356.9 (M+H)+.

後処理

  1. washwashed with water
  2. customabsorbed on silica gel
  3. custompurified
  4. washeluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%)

出典と根拠

ORDレコード
ord-da4f9f5ed4334976a64b3289286ed8a0
出典データセット
uspto-grants-2012_09
特許番号
US08268846B2

反応ノート

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