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Toluene → 4-{2-Amino-6-[(3R)-3-(1-methylethyl)-4-morpholinyl]-4-pyrimidinyl}-2-(ethyloxy)-6-fluorobenzonitrile

HRID 2367606
ノート
印刷プレビュー

反応式

HRID 2367606 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[C:14](F)[C:11]([C:12]#[N:13])=[C:10]([F:17])[CH:9]=2)[CH:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@H:19]2[CH:24]([CH3:26])[CH3:25])[N:3]=1.C1(C)C=CC=CC=1.[CH3:34][CH2:35][O-:36].[Na+]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([F:17])[C:11]([C:12]#[N:13])=[C:14]([O:36][CH2:35][CH3:34])[CH:15]=2)[CH:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@H:19]2[CH:24]([CH3:26])[CH3:25])[N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1140TolueneHCID 2723922Sodium ethoxideHCID 585048264-{2-Amino-6-[(3R)-3-(1-methylethyl)-4-morpholinyl]-4-pyrimidinyl}-2,6-difluorobenzonitrile

生成物 1

HCID 585045594-{2-Amino-6-[(3R)-3-(1-methylethyl)-4-morpholinyl]-4-pyrimidinyl}-2-(ethyloxy)-6-fluorobenzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-{2-Amino-6-[(3R)-3-(1-methylethyl)-4-morpholinyl]-4-pyrimidinyl}-2,6-difluorobenzonitrile (405 mg, 1.12 mmol) was azeotroped with toluene (2×15 mL). The residue was dissolved in 5 mL of DMF as a yellow clear solution, to which was added NaOEt (1.45 mL of a stock solution with concentration of 0.87 mmol/mL, 1.25 mmol, 1.12 equiv) at room temperature in one portion. The resulting light orange clear solution was stirred at room temperature for 20 hours. LCMS showed conversion complete. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography using gradient elution of 1% EtOAc in CHCl3 to 100% EtOAc, providing the title compound (310 mg) as a white solid residue. LC-MS (ES) m/z=386 [M+H]+.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography
  3. washelution of 1% EtOAc in CHCl3 to 100% EtOAc

出典と根拠

ORDレコード
ord-3c843913bae84c38b77181357a669a78
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08697685B2

反応ノート

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