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Sodium Carbonate → 5-(2-(1H-pyrazol-4-yl)ethoxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023321
ノート
印刷プレビュー

反応式

HRID 1023321 の反応式
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][O:8][C:9]2[C:18]3[C:17](=[O:19])[N:16]([CH3:20])[CH:15]=[N:14][C:13]=3[CH:12]=[C:11](Cl)[N:10]=2)[CH:3]=[N:2]1.[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][O:8][C:9]2[C:18]3[C:17](=[O:19])[N:16]([CH3:20])[CH:15]=[N:14][C:13]=3[CH:12]=[C:11]([C:31]3[CH:30]=[CH:29][C:28]([N:25]4[CH2:24][CH2:23][O:22][CH2:27][CH2:26]4)=[CH:33][CH:32]=3)[N:10]=2)[CH:3]=[N:2]1
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 3

HCID 10340Sodium CarbonateHCID 27953614-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholineHCID 866679855-(2-(1H-pyrazol-4-yl)ethoxy)-7-chloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

生成物 1

HCID 669598025-(2-(1H-pyrazol-4-yl)ethoxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

To a solution of 5-(2-(1H-pyrazol-4-yl)ethoxy)-7-chloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (31.6 mg, 0.10 mmol) in 1,4-dioxane (1 mL) were added 4-morpholinophenylboronic acid pinacol ester (29.9 mg, 0.10 mmol), 2M aqueous Na2CO3 solution (155 μL, 0.30 mmol), and a catalytic amount of Pd(dppf)2Cl2. The reaction mixture was purged with N2 and heated at 140° C. by a microwave reactor for 15 minutes. The mixture was then cooled, quenched with H2O and extracted with EtOAc. The combined organic layer was dried over MgSO4, concentrated, and purified by silica gel chromatography (eluent: 0-10% MeOH in DCM) to provide the title compound as a yellow solid. 1H NMR (CD3OD, 400 MHz) δ 8.37 (s, 1H), 8.06 (d, J=9.2 Hz, 2H), 7.71 (s, 2H), 7.43 (s, 1H), 7.04 (d, J=9.2 Hz, 2H), 4.71 (t, J=6.4 Hz, 2H), 3.85 (t, J=4.8 Hz, 4H), 3.55 (s, 3H), 3.27 (t, J=4.8 Hz, 4H), 3.10 (t, J=6.4 Hz, 2H); ESI-MS m/z 433.1 (MH+).

後処理

  1. customThe reaction mixture was purged with N2
  2. temperatureThe mixture was then cooled
  3. customquenched with H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (eluent: 0-10% MeOH in DCM)

出典と根拠

ORDレコード
ord-8afbf1c9a60b416084595086b85f9cbc
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722692B2

反応ノート

読み込み中…

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