Water → 1-Butyl-5-(4-fluorophenyl)-6-hydroxymethyl-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidine

HRID 1885714노트

반응식

HRID 1885714 반응식
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([N:15]1[C:20]2[N:21]=[C:22]([CH:37]([CH3:39])[CH3:38])[C:23]([C:32](OCC)=[O:33])=[C:24]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:19]=2[C:18](=[O:40])[NH:17][C:16]1=[O:41])[CH2:12][CH2:13][CH3:14].[H-].C([Al+]CCCC)CCC.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:11]([N:15]1[C:20]2[N:21]=[C:22]([CH:37]([CH3:38])[CH3:39])[C:23]([CH2:32][OH:33])=[C:24]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:19]=2[C:18](=[O:40])[NH:17][C:16]1=[O:41])[CH2:12][CH2:13][CH3:14]

참가 물질

7

반응물 4

HCID 962WaterHCID 198796871-Butyl-6-ethoxycarbonyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidineHCID 21225700DiisobutylaluminumhydrideHCID 21879971Dibutylaluminium hydride

생성물 1

HCID 198796961-Butyl-5-(4-fluorophenyl)-6-hydroxymethyl-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidine

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8857Ethyl Acetate용매

실험 절차

135 ml of a 1 molar solution of diisobutylaluminum hydride in toluene are slowly added under argon to a suspension of 19.2 g (45 mmol) of the compound from Example 3 in 400 ml of toluene at -75° C., which leads to a clear solution. After 1 hour, a further 30 ml of dibutylaluminum hydride solution are added at the same temperature, the mixture is stirred for a further hour and then allowed to warm to room temperature, 400 ml of water and 200 ml of ethyl acetate being added cautiously from -30° C. The mixture is filtered off with suction through kieselguhr and subsequently washed with ethyl acetate. After phase separation, the aqueous phase is extracted with ethyl acetate, and the combined organic phases are washed with sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed in a column (φ 6 cm) on 500 g of 230-400 mesh silica gel using petroleum ether/ethyl acetate (2:1).

후처리

  1. filtrationThe mixture is filtered off with suction through kieselguhr
  2. washsubsequently washed with ethyl acetate
  3. customAfter phase separation
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washthe combined organic phases are washed with sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed in a column (φ 6 cm) on 500 g of 230-400 mesh silica gel

출처 및 근거

ORD 기록
ord-226a5bb4abdb4398b650089c15febf8e
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05145959

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