Trifluoroacetic acid → HCID 178491938, 화합물

HRID 1243188노트

반응식

HRID 1243188 반응식
C([Si](C)(C)[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:18]3=[N:19][C:20]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=4)=[N:21][CH:22]=[C:17]3[CH2:16][N:15]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[C:14]2=[O:42])[CH2:9][CH2:8]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([N:15]2[CH2:16][C:17]3[C:18](=[N:19][C:20]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=4)=[N:21][CH:22]=3)[N:13]([C@H:10]3[CH2:11][CH2:12][C@H:7]([OH:6])[CH2:8][CH2:9]3)[C:14]2=[O:42])=[CH:35][CH:36]=1

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 178491940HCID 178491940, 화합물

생성물 1

HCID 178491938HCID 178491938, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 1-[trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(4-methoxy-phenyl)-7-(3,4-dimethoxy-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (90 mg, 0.24 mmol) (from Example 19b supra) in dichloromethane (5 mL) was added trifluoroacetic acid (2.0 mL) (Aldrich) at 0° C. The mixture was stirred at 0° C. for 2 hours. The reaction mixture was diluted with ethyl acetate (15 mL) and washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate to give crude product which was recrystallized from ethyl acetate-hexanes to give 3-(4-methoxy-phenyl)-1-(trans-4-hydroxy-cyclohexyl)-7-(3,4-dimethoxy-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 41 mg, 59%).

후처리

  1. washwashed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate
  7. customto give crude product which
  8. customwas recrystallized from ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-3beeb17964d449c382b53190fe6f7d02
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115740B2

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