Triethylamine → (+/-)-[trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-{2-chloro-5-[(4-ethyl-phenylamino)-methyl]-pyrimidin-4-yl}-amine

HRID 1243227ノート

反応式

HRID 1243227 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C(N(CC)CC)C.[C:26]([Si:30]([CH3:39])([CH3:38])[O:31][C@H:32]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33]1)([CH3:29])([CH3:28])[CH3:27]>C(O)CCC>[C:26]([Si:30]([CH3:39])([CH3:38])[O:31][C@H:32]1[CH2:36][CH2:35][C@H:34]([NH:37][C:6]2[C:5]([CH2:9][NH:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=3)=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:33]1)([CH3:29])([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11426039(2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amineHCID 58715071(+/-)-trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

生成物 1

HCID 86594647(+/-)-[trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-{2-chloro-5-[(4-ethyl-phenylamino)-methyl]-pyrimidin-4-yl}-amine

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

(2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amine (200 mg, 0.71 mmol) (from Example 38c supra) was dissolved in hot n-butanol (2 mL) (Aldrich). After cooling to room temperature, triethylamine (0.20 mL, 0.92 mmol) (Allied Signal) and (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine (198 mg, 0.91 mmol) (from Example 9c supra) were successively added and the mixture was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and purified by flash chromatography (20% ethyl acetate in hexanes) to give (±)-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-{2-chloro-5-[(4-ethyl-phenylamino)-methyl]-pyrimidin-4-yl}-amine as a viscous oil. (Yield 272 mg, 84%).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography (20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-b750569661fd4a9cb7e78d37530d5c96
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

読み込み中…