Sodium Carbonate → 2-(4-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)phenyl)acetonitrile

HRID 1484834

반응식

HRID 1484834 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32]#[N:33])=[CH:27][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][C:32]#[N:33])=[CH:27][CH:26]=4)[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]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 58169118HCID 58169118, 화합물

생성물 1

HCID 509432122-(4-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)phenyl)acetonitrile수율 10.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (200 mg, 0.85 mmol, 1.0 equiv.), 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (250 mg, 1.0 mmol, 1.2 equiv.), Pd(dippf)Cl2 (69.5 mg, 0.085 mmol, 0.1 equiv.), Na2CO3 (360.4 mg, 3.4 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 60:1) to afford title compound 2-(4-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)phenyl)acetonitrile (Compound 17) (28.6 mg, 10%) as solid. LC-MS (m/z)=317.1 [M+H]+;

후처리

  1. additionwas added to the filtrate
  2. customThe residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 60:1)

출처 및 근거

ORD 기록
ord-601568d50e1e4aa4b23c4ac4cca85d56
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422271B2

연결된 노트

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