Potassium Carbonate → 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N,N-diethyl-4-methylbenzamide

HRID 2243751노트

반응식

HRID 2243751 반응식
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[N:10]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])[C:11](=[O:14])[NH:12][CH2:13][C:3]=12.[CH2:23]([N:25]([CH2:44][CH3:45])[C:26](=[O:43])[C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=1)[CH3:24].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[F:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[N:10]1[C:4]2[N:5]=[C:6]([S:8][CH3:9])[N:7]=[C:2]([C:29]3[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=3[CH3:33])[C:26]([N:25]([CH2:44][CH3:45])[CH2:23][CH3:24])=[O:43])[C:3]=2[CH2:13][NH:12][C:11]1=[O:14]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 575305005-Chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneHCID 68587202N,N-diethyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

생성물 1

HCID 592079853-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N,N-diethyl-4-methylbenzamide

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

5-chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (0.720 g, 2.1 mmol), N,N-diethyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide from above (1.09 g, 3.15 mmol), and K2CO3 (0.868 g, 6.3 mmol), were taken up in dioxane (42 mL) and water (8.5 mL). The mixture was degassed with argon for 30 min and tetrakis-(triphenylphosphine)palladium(0) (0.183 g, 0.15 mmol) was added. The mixture was then heated under argon at 950 C for 18 h. The solvents were pumped off and after aqueous workup, the crude material was flashed on silica gel (150 g) eluted with a EtOAc/CH2Cl2 gradient to give the title compound as a white amorphous solid. mp 127-129° C. LC-MS m/z 498 (M+H)+, 2.11 min (ret time).

후처리

  1. customThe mixture was degassed with argon for 30 min
  2. temperatureThe mixture was then heated under argon at 950 C for 18 h
  3. washeluted with a EtOAc/CH2Cl2 gradient

출처 및 근거

ORD 기록
ord-a0a5c29b4cf84c3d96acaa028ae53f2a
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674789B2

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