Potassium Carbonate → 5-(3-amino-1,2,4-triazin-6-yl)-N-methylpyridine-2-carboxamide

HRID 452040

反応式

HRID 452040 の反応式
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][N:6]=1)=[O:4].Br[C:21]1[N:26]=[N:25][C:24]([NH2:27])=[N:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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>[NH2:27][C:24]1[N:25]=[N:26][C:21]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[N:6][CH:7]=2)=[CH:22][N:23]=1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 153325646-Bromo-1,2,4-triazin-3-amineHCID 44119560N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide

生成物 1

HCID 575165335-(3-amino-1,2,4-triazin-6-yl)-N-methylpyridine-2-carboxamide収率 45.7%

試薬・触媒・溶媒 4

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

反応条件

温度
120 °C

実験手順

A mixture of N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (200 mg, 0.80 mmol) (VWR, Cat. #200068-640), 6-bromo-1,2,4-triazin-3-amine (130 mg, 0.76 mmol, Example 2, Step 1), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.04 mmol) and potassium carbonate (0.32 g, 2.3 mmol) in toluene (1.3 mL), ethanol (0.66 mL) and water (0.66 mL) was heated at 120° C. for 1.5 h. The mixture was filtered and washed with methanol. The filtrate was purified by RP-HPLC (pH=10) to afford the desired product (80 mg, 45.54%). LCMS (M+H)+: m/z=231.4; LCMS (M+H+H2O)+: m/z=249.3.

後処理

  1. filtrationThe mixture was filtered
  2. washwashed with methanol
  3. customThe filtrate was purified by RP-HPLC (pH=10)

出典と根拠

ORDレコード
ord-e5414436b6254139a962e9e0923cb320
出典データセット
uspto-grants-2013_07
特許番号
US08487096B2

関連ノート

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