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

HRID 1243230ノート

反応式

HRID 1243230 の反応式
C([Si](C)(C)[O:6][C@H:7]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:17]3=[N:18][C:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[N:20][CH:21]=[C:16]3[CH2:15][N:14]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][CH:31]=3)[C:13]2=[O:38])[CH2:8]1)(C)(C)C.N1C=CC=CC=1.F>N1C=CC=CC=1>[CH2:36]([C:33]1[CH:34]=[CH:35][C:30]([N:14]2[CH2:15][C:16]3[C:17](=[N:18][C:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[N:20][CH:21]=3)[N:12]([C@H:9]3[CH2:10][CH2:11][C@H:7]([OH:6])[CH2:8]3)[C:13]2=[O:38])=[CH:31][CH:32]=1)[CH3:37]

参加物

4

反応物 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 69584210(+/-)-1-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

生成物 1

HCID 69582145(+/-)-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-1-(trans-3-hydroxy-cyclopentyl)-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

A solution of (±)-1-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (47 mg, 0.08 mmol) in pyridine (1 mL) (Fisher) was treated at room temperature with hydrogen fluoride-pyridine (0.6 mL) (Aldrich) for 20 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 (±)-3-(4-ethyl-phenyl)-7-(4-fluoro-phenylamino)-1-(trans-3-hydroxy-cyclopentyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid. (Yield 32 mg, 87%).

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-8a2ca0131da049f3a9c5362d066d6f68
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…