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 2243751ノート

反応式

HRID 2243751 の反応式
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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a0a5c29b4cf84c3d96acaa028ae53f2a
出典データセット
uspto-grants-2010_03
特許番号
US07674789B2

反応ノート

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