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Ethyl Acetate → tert-butyl(3S)-3-{[6-chloro-5-(2-hydroxyethyl)-2-(methylsulfanyl)pyrimidin-4-yl]amino}-3-methylpyrrolidine-1-carboxylate

HRID 1775490
ノート
印刷プレビュー

反応式

HRID 1775490 の反応式
Cl[C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.[NH2:14][C@@:15]1([CH3:27])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]1.CCN(C(C)C)C(C)C.CCOC(C)=O>CS(C)=O>[Cl:11][C:6]1[N:5]=[C:4]([S:12][CH3:13])[N:3]=[C:2]([NH:14][C@@:15]2([CH3:27])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]2)[C:7]=1[CH2:8][CH2:9][OH:10]
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 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 86328910(S)-t-Butyl 3-amino-3-methylpyrrolidine-1-carboxylateHCID 1184361184,6-Dichloro-2-(methylthio)-5-pyrimidineethanol

生成物 1

HCID 118436348tert-butyl(3S)-3-{[6-chloro-5-(2-hydroxyethyl)-2-(methylsulfanyl)pyrimidin-4-yl]amino}-3-methylpyrrolidine-1-carboxylate収率 65%

試薬・触媒・溶媒

1
HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

To a solution of 2-[4,6-dichloro-2-(methylsulfanyl)pyrimidin-5-yl]ethanol (1.25 g, 5.23 mmol) and tert-butyl(3S)-3-amino-3-methylpyrrolidine-1-carboxylate (1.57 g, 7.84 mmol) in DMSO (13 mL) was added DIEA (4.6 mL, 26.1 mmol) at room temperature. The reaction mixture was stirred at 110° C. for 42 h, whereupon the mixture was poured into EtOAc and washed with water. The water layer was extracted with EtOAc (3 times). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified via ISCO normal phase silica gel chromatography (80 g column) eluting with a 0-100% gradient of EtOAc/Heptane to give the title compound (1.37 g, 65%) as a light yellow-white foamy solid. 1H NMR (400 MHz, DMSO-d6) δ 6.96 (d, J=17.0 Hz, 1 H), 5.06 (br s, 1 H), 3.75 (dd, J=20.6, 11.2 Hz, 1 H), 3.54 (br s, 2 H), 3.50-3.33 (m, 3 H), 2.77 (t, J=6.3 Hz, 2 H), 2.44 (s, 3 H), 2.40-2.23 (m, 1 H), 2.03-1.93 (m, 1 H), 1.47 (d, J=11.1 Hz, 3 H), 1.38 (d, J=13.4 Hz, 9 H). m/z (APCI+) for C17H27ClN4O3S 403.9 (M+H)+.

後処理

  1. washwashed with water
  2. extractionThe water layer was extracted with EtOAc (3 times)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via ISCO normal phase silica gel chromatography (80 g column)
  8. washeluting with a 0-100% gradient of EtOAc/Heptane

出典と根拠

ORDレコード
ord-1d00e76304f44a10b56cf2471b4d47e8
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09260439B2

反応ノート

読み込み中…

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