1-Benzyl-1H-pyrazole-4-boronic acid → 5-(1-Benzyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-ylamine

HRID 1054424

反応式

HRID 1054424 の反応式
CS[C:3]1[N:8]2[N:9]=[C:10]([NH2:12])[N:11]=[C:7]2[CH:6]=[CH:5][N:4]=1.[CH2:13]([N:20]1[CH:24]=[C:23](B(O)O)[CH:22]=[N:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.S1C=CC=C1C([O-])=O.[Cu+].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>[CH2:13]([N:20]1[CH:24]=[C:23]([C:3]2[N:8]3[N:9]=[C:10]([NH2:12])[N:11]=[C:7]3[CH:6]=[CH:5][N:4]=2)[CH:22]=[N:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 2

HCID 33528811-Benzyl-1H-pyrazole-4-boronic acidHCID 595895295-Methylsulfanyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-ylamine

生成物 1

HCID 595895835-(1-Benzyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-ylamine

試薬・触媒・溶媒 3

HCID 11194830Cuprous 2-thiophenecarboxylate触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
130 °C

実験手順

A microwave vial containing 5-methylsulfanyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-ylamine (0.05 g, 0.276 mmol), 1-benzyl-1H-pyrazole-4-boronic acid (123 mg, 0.607 mmol), copper(I)thiophene carboxylate (116 mg, 0.607 mmol) and tetrakis(triphenylphosphine)palladium (33 mg, 0.028 mmol) in THF (1.2 mL) was heated under microwave irradiation (130° C., 15 min). The reaction mixture was filtered through celite and the cake washed with dichloromethane. The filtrate was washed with water followed by brine, dried over magnesium sulfate and concentrated under vacuum. Trituration with diethyl ether provided a yellow solid that did not require further purification. Yield: 0.05 g, 63%; LCMS method: 2, RT: 3.18 min, MI: 292 [M+1].

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe cake washed with dichloromethane
  3. washThe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customTrituration with diethyl ether provided a yellow solid that
  7. custompurification

出典と根拠

ORDレコード
ord-913f62aa73c046fca213e8f2cf00bfe2
出典データセット
uspto-grants-2016_07
特許番号
US09394301B2

関連ノート

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