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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
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HRID 1023321 반응식
[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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

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

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온도
140 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-8afbf1c9a60b416084595086b85f9cbc
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722692B2

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