Chloroform → (R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(pyrrolidin-1-yl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

HRID 44849ノート

反応式

HRID 44849 の反応式
Br[C:2]1[N:3]([C:7]2[N:16]=[CH:15][C:14]3[N:13]([CH3:17])[C:12](=[O:18])[C@@H:11]([CH2:19][CH3:20])[N:10]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[C:9]=3[N:8]=2)[CH:4]=[CH:5][N:6]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.C(Cl)(Cl)Cl.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:21]1([N:10]2[C:9]3[N:8]=[C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[N:16]=[CH:15][C:14]=3[N:13]([CH3:17])[C:12](=[O:18])[C@H:11]2[CH2:19][CH3:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

9

反応物 5

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 58405307(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

生成物 1

HCID 58405679(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(pyrrolidin-1-yl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one収率 38.3%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65, 150 mg, 0.37 mmol), pyrrolidine (52 mg, 0.74 mmol), Pd2dba3.CHCl3 (76 mg, 0.074 mmol), BINAP (69 mg, 0.11 mmol) and K2CO3 (153 mg, 1.11 mmol) were dissolved in 1 mL of degassed t-BuOH and the resulting solution was heated at 130° C. for 18 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic extracts were dried with Na2SO4, filtered and evaporated, and the residue was purified by preparative HPLC to give the title compound (56 mg). LCMS: 396.2 m/z (M+H)+; ret. Time: 2.76 min (Analytical Method A).

後処理

  1. washwashed with brine
  2. dry with materialThe organic extracts were dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-b4594beaad694721a1b74d411a3f9d6f
出典データセット
uspto-grants-2013_09
特許番号
US08541418B2

反応ノート

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