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Triethylamine → 2-[1-(1-Dimethylphosphonopiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]-pyrimidine

HRID 2268962
ノート
印刷プレビュー

反応式

HRID 2268962 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1.C(N(CC)CC)C.[P:32](Cl)([O:36][CH3:37])([O:34][CH3:35])=[O:33]>C(Cl)Cl.CCOC(C)=O>[CH3:35][O:34][P:32]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1)([O:36][CH3:37])=[O:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 101863Phosphorochloridic acid, dimethyl esterHCID 183326302-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

生成物 1

HCID 701386792-[1-(1-Dimethylphosphonopiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]-pyrimidine収率 69.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (44 mg, 0.136 mmol) in CH2Cl2 (1.5 mL) was added triethylamine (29 μL, 0.204 mmol) followed by dimethyl chlorophosphate (22 μL, 0.204 mmol) at 0° C. After stirring 30 min at 0° C., the reaction mixture was diluted with EtOAc (10 mL) and was washed with saturated aqueous NaHCO3 followed by brine. The organic layer was dried over Na2SO4. After removal of the solvent, the crude product was purified by preparative thin layer chromatography (3:1 acetone:hexane) to obtain 40.6 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.36 (br s, 1H); 8.14 (d, J=7.3 Hz, 1H); 7.83 (d, J=7.3 Hz, 1H); 7.38 (m, 2H); 6.78 (d, J=5.4 Hz, 1H); 4.15 (m, 1H); 3.67 (s, 3H); 3.65 (s, 3H); 1.28 (d, J=6.5 Hz, 3H). Mass spectrum 431.3 (ESI, M+1).

後処理

  1. washwas washed with saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customAfter removal of the solvent
  4. customthe crude product was purified by preparative thin layer chromatography (3:1 acetone:hexane)

出典と根拠

ORDレコード
ord-11d3078afa6f454ca62ac06c036457be
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06329380B1

反応ノート

読み込み中…

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