6-chloro-N-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-5-nitropyrimidin-4-amine → HCID 58577325、化合物

HRID 587564ノート

反応式

HRID 587564 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[N:20]([CH3:21])[C:19]4[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=4[N:17]=3)=[CH:11][CH:10]=2)[C:3]=1[N+:26]([O-])=O>[Pd].CO.C1COCC1>[CH3:21][N:20]1[C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[N:17]=[C:16]1[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:4]2[C:3]([NH2:26])=[CH:2][N:7]=[CH:6][N:5]=2)=[CH:10][CH:11]=1

参加物

5

反応物 1

HCID 585776716-chloro-N-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-5-nitropyrimidin-4-amine

生成物 1

HCID 58577325HCID 58577325、化合物収率 39.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6-chloro-N-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-5-nitropyrimidin-4-amine (240 mg) and 10% palladium on carbon (160 mg) in MeOH (10 mL) and THF (10 mL) was hydrogenated under balloon pressure at room temperature overnight. To the mixture was added TEA (0.50 mL). The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-5% MeOH in AcOEt) to give N4-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}pyrimidine-4,5-diamine (80 mg) as a colorless solid.

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with 0%-5% MeOH in AcOEt)

出典と根拠

ORDレコード
ord-adfabb533a5746c5a81828324320aab3
出典データセット
uspto-grants-2016_01
特許番号
US09226921B2

反応ノート

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