Sodium Carbonate → 5-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023318노트

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HRID 1023318 반응식
Cl[C:2]1[N:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:9]2[C:8](=[O:22])[N:7]([CH3:23])[CH:6]=[N:5][C:4]=2[CH:3]=1.[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][CH:31]=2)[CH2:26][CH2:25]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]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][O:12][C:10]2[C:9]3[C:8](=[O:22])[N:7]([CH3:23])[CH:6]=[N:5][C:4]=3[CH:3]=[C:2]([C:33]3[CH:32]=[CH:31][C:30]([N:27]4[CH2:26][CH2:25][O:24][CH2:29][CH2:28]4)=[CH:35][CH:34]=3)[N:11]=2)=[CH:15][CH:16]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27953614-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholineHCID 866679837-chloro-5-(4-methoxybenzyloxy)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

생성물 1

HCID 681078795-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

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온도
140 °C

실험 절차

To a solution of 7-chloro-5-(4-methoxybenzyloxy)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (750 mg, 2.26 mmol) in 1,4-dioxane (11 mL) were added 4-morpholinophenylboronic acid pinacol ester (654 mg, 2.26 mmol), 2M aqueous Na2CO3 solution (3.39 mL, 6.78 mmol), and Pd(dppf)2Cl2 (36.9 mg, 0.045 mmol). 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 (100 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic layer was dried over MgSO4 and evaporated under reduced pressure to afford crude 5-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one.

후처리

  1. customThe reaction mixture was purged with N2
  2. temperatureThe mixture was then cooled
  3. customquenched with H2O (100 mL)
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-a86b379a273b41e59f6b27681b101ee3
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722692B2

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