2-Phenylpyrimidin-5-amine → HCID 66586937、化合物

HRID 2406070

反応式

HRID 2406070 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[C:19]1([C:25]2[N:30]=[CH:29][C:28]([NH2:31])=[CH:27][N:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1.O>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:9][C:5]=1[C:6]([NH:31][C:28]1[CH:29]=[N:30][C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:26][CH:27]=1)=[O:8])([O-:3])=[O:2]

参加物

7

反応物 3

HCID 7865652-Phenylpyrimidin-5-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 144593312-Nitro-5-(piperidin-1-yl)benzoic acid

生成物 1

HCID 66586937HCID 66586937、化合物収率 12.7%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

Into a 50-mL round-bottom flask, was placed a solution of 2-nitro-5-(piperidin-1-yl)benzoic acid (1.096 g, 4.38 mmol, 1.50 equiv) in dichloromethane (20 mL), 2-phenylpyrimidin-5-amine (500 mg, 2.92 mmol, 1.00 equiv), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (838 mg, 4.39 mmol, 1.50 equiv), and 4-dimethylaminopyridine (713 mg, 5.84 mmol, 2.00 equiv). The resulting solution was stirred overnight at 25° C. The reaction was diluted with 100 mL of water and the resulting mixture was extracted with 3×50 mL of dichloromethane. The organic layers were combined, washed with 1×100 mL of brine, dried over sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with PE:EA:CH2Cl2 (20:1:0-3:1:1). The product was obtained as 150 mg (11%) of a yellow solid.

後処理

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionthe resulting mixture was extracted with 3×50 mL of dichloromethane
  3. washwashed with 1×100 mL of brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. washeluted with PE

出典と根拠

ORDレコード
ord-2a384607d0ac4284a2cd1c8f056eb2eb
出典データセット
uspto-grants-2014_08
特許番号
US08809339B2

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