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

HRID 452040

반응식

HRID 452040 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e5414436b6254139a962e9e0923cb320
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487096B2

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