N-methyl-2-pyrrolidone → 5-{8-[(3S)-3-Ethylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

HRID 1876572ノート

反応式

HRID 1876572 の反応式
C(N(C(C)C)CC)(C)C.CN1CCCC1=O.[CH2:17]([C@H:19]1[CH2:24][NH:23][CH2:22][CH2:21][NH:20]1)[CH3:18].[NH2:25][C:26]1[N:31]=[CH:30][C:29]([C:32]2[N:40]=[C:39]3[C:35]([N:36]=[C:37](Cl)[N:38]3[CH2:41][C:42]([F:45])([F:44])[F:43])=[C:34]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)[N:33]=2)=[CH:28][N:27]=1>O>[CH2:17]([C@@H:19]1[NH:20][CH2:21][CH2:22][N:23]([C:37]2[N:38]([CH2:41][C:42]([F:43])([F:45])[F:44])[C:39]3[C:35]([N:36]=2)=[C:34]([N:47]2[CH2:48][CH2:49][O:50][CH2:51][CH2:52]2)[N:33]=[C:32]([C:29]2[CH:28]=[N:27][C:26]([NH2:25])=[N:31][CH:30]=2)[N:40]=3)[CH2:24]1)[CH3:18]

参加物

6

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 11240458(2S)-2-EthylpiperazineHCID 593335342-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine

生成物 1

HCID 593335585-{8-[(3S)-3-Ethylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine収率 81.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

Diisopropylethylamine (1.48 ml, 8.49 mmol) was added to an N-methyl-2-pyrrolidone suspension (4 ml) of 2-(S)-ethylpiperazine 2 hydrochloride (529 mg, 2.83 mmol) and 2-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine (391 mg, 0.94 mmol) and the resulting mixture was stirred at 100° C. for 4 days. Water was added to the reaction mixture and the resulting mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (chloroform:methanol=97:3 to 90:10) to give the title compound (379 mg) as a pale yellow solid.

後処理

  1. extractionthe resulting mixture was extracted twice with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationthe mixture was filtrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel chromatography (chloroform:methanol=97:3 to 90:10)

出典と根拠

ORDレコード
ord-f92a75927ad84e5cacc667cfc3288593
出典データセット
uspto-grants-2012_11
特許番号
US08309546B2

反応ノート

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