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Water → tert-butyl 3-({6-chloro-5-(2-hydroxyethyl)-2-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl}amino)azetidine-1-carboxylate

HRID 1775460
ノート
印刷プレビュー

反応式

HRID 1775460 の反応式
Cl[C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([Cl:11])[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=1.[C:19]([O:23][C:24]([N:26]1[CH2:29][CH:28]([NH2:30])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:11][C:6]1[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=[C:2]([NH:30][CH:28]2[CH2:27][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:29]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 962WaterHCID 81531DiisopropylethylamineHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 1184366042-{4,6-dichloro-2-[(3S)-3-methylmorpholin-4-yl]pyrimidin-5-yl}ethanol

生成物 1

HCID 118436480tert-butyl 3-({6-chloro-5-(2-hydroxyethyl)-2-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl}amino)azetidine-1-carboxylate収率 86.2%

試薬・触媒・溶媒

1
HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
75 °C

実験手順

A solution of 2-{4,6-dichloro-2-[(3S)-3-methylmorpholin-4-yl]pyrimidin-5-yl}ethanol (as prepared in Preparation 2)(0.652 g, 2.23 mmol) and 3-amino-azetidine-1-carboxylic acid tert-butyl ester (0.5 g, 2.9 mmol) in DMSO (10.0 mL) was treated with DIPEA (0.7 mL, 4 mmol) and heated at 75° C. for 5 days in a sealed tube. The mixture was poured into a flask containing water and the resulting solids were collected by filtration and rinsed with water. The solids were taken up in DCM, dried over MgSO4 and filtered. The filtrate was purified directly by silica gel chromatography using a gradient of 25-100% EtOAc/heptane as eluent to give 0.823 g (86%) of the title compound as a crisp foam. 1H NMR (400 MHz, DMSO-d6) δ 7.30 (d, J=5.6 Hz, 1 H), 4.71 (t, J=5.2 Hz, 1 H), 4.62-4.53 (m, 1 H), 4.47-4.40 (m, 1 H), 4.13-4.04 (m, 3 H), 3.89-3.78 (m, 3 H), 3.66 (d, J=11.4 Hz, 1 H), 3.55-3.44 (m, 3 H), 3.36 (dt, J=11.7, 2.9 Hz, 1 H), 3.04 (dt, J=12.9, 3.7 Hz, 1 H), 2.69 (t, J=6.9 Hz, 2 H), 1.39 (s, 9 H), 1.14 (d, J=6.7 Hz, 3 H).

後処理

  1. additionThe mixture was poured into a flask
  2. filtrationthe resulting solids were collected by filtration
  3. washrinsed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was purified directly by silica gel chromatography

出典と根拠

ORDレコード
ord-f6ebe5c077ec4049b1c1b8e4b8528261
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

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