Diisopropylethylamine → (4-tert-Butyl-phenyl)-[7-(3-methanesulfonyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-amine

HRID 971199ノート

反応式

HRID 971199 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH2:21][CH2:20][NH:19][CH2:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:23]1[C:28]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH2:21][CH2:20][N:19]([C:23]4[C:28]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 125137462-Chloro-3-(methanesulfonyl)pyridineHCID 59021490N-(4-tert-butylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

生成物 1

HCID 12004320(4-tert-Butyl-phenyl)-[7-(3-methanesulfonyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-amine収率 48.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

A mixture of N-(4-tert-butylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (0.066 g, 0.23 mmol), 2-chloro-3-(methylsulfonyl)pyridine (Ponticello et al, J. Org. Chem., 44(17), 1979), (0.088 g, 0.47 mmol) and N,N-diisopropylethlamine (0.041 mL, 0.23 mmol) was heated in a sealed tube via microwave (Emrys Optimizer model, Personal Chemistry) for 30 min at 150° C. The reaction mixture was cooled to r.t. and poured into water (20 mL). The mixture was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated to leave an oil which was purified by silica gel chromatography (ethyl acetate/hexane gradient) to give the title compound as a white solid (0.049 g).

後処理

  1. temperatureThe reaction mixture was cooled to r.t.
  2. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto leave an oil which
  7. customwas purified by silica gel chromatography (ethyl acetate/hexane gradient)

出典と根拠

ORDレコード
ord-a01ef1da6a5849709e116f043408736a
出典データセット
uspto-grants-2007_12
特許番号
US07312330B2

反応ノート

読み込み中…