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

HRID 1508284노트

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HRID 1508284 반응식
[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

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b3a220ae900d4b86badfeb4bca7de013
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221824B2

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