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 1243226노트

반응식

HRID 1243226 반응식
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]

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-99037ab23f4a436094b4af1af2e73bfd
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115740B2

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