Potassium Carbonate → 4-(3-amino-1,2,4-triazin-6-yl)-N,2-dimethylbenzamide

HRID 452042ノート

反応式

HRID 452042 の反応式
[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]=1[CH3:19].Br[C:22]1[N:27]=[N:26][C:25]([NH2:28])=[N:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.CO.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>[NH2:28][C:25]1[N:26]=[N:27][C:22]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:2][CH3:1])=[O:20])=[C:5]([CH3:19])[CH:6]=2)=[CH:23][N:24]=1

参加物

9

反応物 3

HCID 11430Potassium CarbonateHCID 153325646-Bromo-1,2,4-triazin-3-amineHCID 57516536N,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

生成物 1

HCID 575165354-(3-amino-1,2,4-triazin-6-yl)-N,2-dimethylbenzamide収率 45.2%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

A mixture of N,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Step 2, 0.3 g, 0.001 mol), 6-bromo-1,2,4-triazin-3-amine (0.21 g, 1.2 mmol, Example 2, Step 1), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol) and potassium carbonate (0.45 g, 3.3 mmol) in toluene (1.9 mL), ethanol (0.94 mL) and water (0.94 mL). The resulting mixture was heated at 130° C. for 2.5 h. The mixture was diluted with MeOH, filtered, and washed with DCM/methanol (90%). The filtrate was concentrated. The residue was purified by flash chromatography on a silica gel column with 10% MeOH in DCM to afford the desired product (110 mg, 41%). LCMS (M+H)+: m/z=244.3.

後処理

  1. filtrationfiltered
  2. washwashed with DCM/methanol (90%)
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by flash chromatography on a silica gel column with 10% MeOH in DCM

出典と根拠

ORDレコード
ord-abc0bf1818d4434e95d3f929d6adc733
出典データセット
uspto-grants-2013_07
特許番号
US08487096B2

反応ノート

読み込み中…