Pyridine, hydrofluoride (1:1) → (R)-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-1-(2-hydroxy-1-methyl-ethyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 1243226ノート

反応式

HRID 1243226 の反応式
C([Si](C)(C)[O:6][CH2:7][C@H:8]([N:10]1[C:15]2=[N:16][C:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:18][CH:19]=[C:14]2[CH2:13][N:12]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][CH:29]=2)[C:11]1=[O:36])[CH3:9])(C)(C)C.N1C=CC=CC=1.F>N1C=CC=CC=1>[CH2:34]([C:31]1[CH:32]=[CH:33][C:28]([N:12]2[CH2:13][C:14]3[C:15](=[N:16][C:17]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[N:18][CH:19]=3)[N:10]([C@H:8]([CH3:9])[CH2:7][OH:6])[C:11]2=[O:36])=[CH:29][CH:30]=1)[CH3:35]

参加物

4

反応物 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 11364631(R)-1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

生成物 1

HCID 11362184(R)-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-1-(2-hydroxy-1-methyl-ethyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

(R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (100 mg, 0.18 mmol) (from Example 38f supra) in pyridine (1.5 mL) (Fisher) was treated at room temperature with hydrogen fluoride-pyridine (0.6 mL) (Aldrich) for 15 minutes. The reaction mixture was quenched with 1 N aqueous hydrochloric acid at 0° C., then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (50% ethyl acetate in hexanes) to give (R)-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-1-(2-hydroxy-1-methyl-ethyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a colorless viscous oil. (Yield 45 mg, 61%).

後処理

  1. customThe reaction mixture was quenched with 1 N aqueous hydrochloric acid at 0° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-99037ab23f4a436094b4af1af2e73bfd
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

読み込み中…