Tetrahydrofuran → HCID 86686212, 화합물

HRID 2171641

반응식

HRID 2171641 반응식
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C1COCC1.C([Li])CCC.CCCCCC.[N:33]1([C:39]2[N:44]=[CH:43][C:42]([CH:45]=[O:46])=[CH:41][N:40]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CCOC(C)=O.O>[Si:7]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:45]([C:42]2[CH:43]=[N:44][C:39]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[N:40][CH:41]=2)[OH:46])[CH:16]=[CH:15][CH:14]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 31609782-(Morpholin-4-yl)pyrimidine-5-carbaldehydeHCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 86686212HCID 86686212, 화합물수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

[(3-Bromobenzyl)oxy](tert-butyl)dimethylsilane (860 mg) was mixed with THF (10 ml), followed by cooling to −78° C. under argon atmosphere. A 1.60M n-butyl lithium/hexane solution (1.8 ml) was added dropwise thereto, followed by stirring at −78° C. for 10 minutes, and then 2-morpholin-4-ylpyrimidine-5-carboaldehyde (500 mg) was added thereto. The mixture was warmed to 0° C. over 1 hour and then stirred again at 0° C. for 1 hour. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain [3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol (914 mg).

후처리

  1. temperatureThe mixture was warmed to 0° C. over 1 hour
  2. stirringstirred again at 0° C. for 1 hour
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-052ef783d09147179497a9afc818aad1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051283B2

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