Water → 4-(2-Chloro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811827ノート

反応式

HRID 1811827 の反応式
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[Cl:10][C:11]1[C:16](B(O)O)=[CH:15][C:14]([CH3:20])=[CH:13][N:12]=1.O.C(=O)([O-])[O-].[Na+].[Na+].COCCOC.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][C:11]1[C:16]([C:2]2[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=2)=[CH:15][C:14]([CH3:20])=[CH:13][N:12]=1

参加物

7

反応物 5

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 305914-Chloro-6-methyl-1,3,5-triazin-2-amineHCID 2735133Sodium Carbonate MonohydrateHCID 27631262-Chloro-5-methylpyridine-3-boronic acid

生成物 1

HCID 595482414-(2-Chloro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine収率 44.6%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
90 °C

実験手順

A glass microwave reaction vessel was charged with 4-chloro-6-methyl-1,3,5-triazin-2-amine (0.350 g, 2 mmol), 2-chloro-5-methylpyridin-3-ylboronic acid (combi-blocks catalog number BB-3511) (0.6 g, 3 mmol), sodium carbonate, monohydrate, crystal (J.T. Baker catalog number 3600-01) (0.450 g, 7 mmol), tetrakis(triphenylphosphine)palladium (0) (Strem chemicals catalog number 46-Z150) (0.3 g, 0.2 mmol). Degassed 1,2-dimethoxyethane (Aldrich catalog #255527) (11 mL, 109 mmol) and water (1 mL, 2 mmol) were added to the mixture. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 90° C. for 30 min. The mixture was filtered through Celite® (diatomaceous earth) and washed with ethyl acetate. The crude product was adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (40 g), eluting with a gradient of 5% to 10% 2 M NH3/MeOH in dichloromethane, to provide 4-(2-chloro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.210 g, 36% yield).

後処理

  1. customA glass microwave reaction vessel
  2. filtrationThe mixture was filtered through Celite® (diatomaceous earth)
  3. washwashed with ethyl acetate
  4. customchromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr
  5. wash, pre-packed silica gel column (40 g), eluting with a gradient of 5% to 10% 2 M NH3/MeOH in dichloromethane

出典と根拠

ORDレコード
ord-bc13b176f2874a8bb040db03f8b45c03
出典データセット
uspto-grants-2013_01
特許番号
US08362241B2

反応ノート

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