Diisopropylethylamine → HCID 86730180、化合物

HRID 1850143ノート

反応式

HRID 1850143 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.Cl.C[NH:19][CH2:20][C:21]#[CH:22].[CH:23](N(C(C)C)CC)(C)C>CS(C)=O.CCOC(C)=O>[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:19][C@@H:20]([CH3:23])[C:21]#[CH:22])[N:7]=1)([CH3:15])[CH3:14]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 22416630HCID 22416630、化合物HCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

生成物 1

HCID 86730180HCID 86730180、化合物収率 31%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of compound (S)-3-(2-Chloro-pyrimidin-4-yl)-4-isopropyl-oxazolidin-2-one (1.03 g, 4.3 mmol) in DMSO (12 mL) was added methyl-prop-2-ynylamine HCl salt (450 mg, 4.3 mmol) and diisopropylethylamine (2.2 mL, 12.6 mmol). The reaction was heated to 110 C for 18 hours. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (25 mL) and brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%) provided (S)-4-Isopropyl-3-[2-((S)-1-methyl-prop-2-ynylamino)-pyrimidin-4-yl]-oxazolidin-2-one (360 mg) in 31% yield. LC-MS m/z: 275.1 (M−Boc)+; RT.: 1.33 min.

後処理

  1. temperatureThe reaction was heated to 110 C for 18 hours
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%)

出典と根拠

ORDレコード
ord-259f04e011174aee9ae63a5f71dad13e
出典データセット
uspto-grants-2015_02
特許番号
US08957068B2

反応ノート

読み込み中…