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

HRID 2243748ノート

反応式

HRID 2243748 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.[CH3:23][N:24]([CH3:43])[C:25](=[O:42])[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=1.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:28]3[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=3[CH3:32])[C:25]([N:24]([CH3:43])[CH3:23])=[O:42])[C:3]=2[CH2:13][NH:12][C:11]1=[O:14]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 57416236N,N,4-trimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 575305005-Chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

生成物 1

HCID 119508173-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N,N,4-trimethylbenzamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

5-chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (0.102 g, 0.298 mmol), N,N,4-trimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide from above, (0.129 g, 0.447 mmol), and K2CO3 (0.123 g, 0.894 mmol), were taken up in dioxane (6 mL) and water (1.2 mL). The mixture was degassed with argon for 30 min and tetrakis(triphenyl-phosphine)palladium(0) (0.026 g, 0.022 mmol) was added. The mixture was then heated under argon at 95°C. for 18 h. The solvents were pumped off, and after aqueous workup, the crude material was flashed on silica gel (15 g), eluted with a EtOAc/CH2Cl2 gradient to give the title compound as a white amorphous solid. mp 144-147° C. LC-MS m/z 470 (M+H)+, 2.02 min (ret time).

後処理

  1. customThe mixture was degassed with argon for 30 min
  2. washeluted with a EtOAc/CH2Cl2 gradient

出典と根拠

ORDレコード
ord-50b19d4f53d64072b0601af12d03d95f
出典データセット
uspto-grants-2010_03
特許番号
US07674789B2

反応ノート

読み込み中…