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

HRID 1484836

반응식

HRID 1484836 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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]+).

후처리

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

출처 및 근거

ORD 기록
ord-e84f68b1f54d49de942bbf9481d80bc8
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422271B2

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