Sodium Carbonate → 2-(4-(4-(Benzyloxy)pyrimidin-2-yl)phenyl)acetonitrile

HRID 1484836ノート

反応式

HRID 1484836 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 38429222-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrileHCID 151332374-(Benzyloxy)-2-chloropyrimidine

生成物 1

HCID 581691442-(4-(4-(Benzyloxy)pyrimidin-2-yl)phenyl)acetonitrile収率 31%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-(benzyloxy)-2-chloropyrimidine (3.2 g, 14.5 mmol, 1.0 equiv.), 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (4.2 g, 17.4 mmol, 1.2 equiv.), Pd(dippf)Cl2 (1.18 g, 1.45 mmol, 0.1 equiv.), Na2CO3 (6.1 g, 58 mmol, 4.0 equiv.), dioxane (5 ml) and water (1 ml) was added to the filtrate. The reaction mixture was heated to 100° C. for 15 h under nitrogen atmosphere. The residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 200:1) to afford 2-(4-(4-(benzyloxy)pyrimidin-2-yl)phenyl)acetonitrile (1.3 g, 31%) as white solid. The title compound was determination by LC-MS (LC-MS (m/z)=302.1 [M+H]+).

後処理

  1. additionwas added to the filtrate
  2. customThe residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 200:1)

出典と根拠

ORDレコード
ord-e84f68b1f54d49de942bbf9481d80bc8
出典データセット
uspto-grants-2016_08
特許番号
US09422271B2

反応ノート

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