Hydrochloric Acid → 4-Piperidinemethanol, 1-(7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo(2,3-d)pyrimidin-4-yl)-

HRID 1253832노트

반응식

HRID 1253832 반응식
[BH4-].[Li+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:23]([CH3:24])[C:22](=O)[N:21]([C:26]4[C:31]([CH3:32])=[CH:30][C:29]([Br:33])=[CH:28][C:27]=4[CH3:34])[C:16]=3[N:17]=[C:18]([CH3:20])[N:19]=2)[CH2:10][CH2:9]1)=O)C.Cl.[OH-].[Na+]>O1CCCC1.CO>[Br:33][C:29]1[CH:30]=[C:31]([CH3:32])[C:26]([N:21]2[C:16]3[N:17]=[C:18]([CH3:20])[N:19]=[C:14]([N:11]4[CH2:12][CH2:13][CH:8]([CH2:6][OH:5])[CH2:9][CH2:10]4)[C:15]=3[C:23]([CH3:24])=[CH:22]2)=[C:27]([CH3:34])[CH:28]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 59845595HCID 59845595, 화합물

생성물 1

HCID 104785674-Piperidinemethanol, 1-(7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo(2,3-d)pyrimidin-4-yl)-수율 86.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of lithium borohydride (2.61 g) in tetrahydrofuran (60 mL) was added a solution of 1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-4-carboxylic acid ethyl ester (6.0 g) in a mixture of tetrahydrofuran (60 mL) and methanol (3 mL) dropwise over 10 minutes under ice-cooling. The reaction mixture was warmed up to room temperature and stirred for 3 hours. After cooling with an ice-bath, 6 M HCl aqueous solution (30 mL) was added and stirred at room temperature for 1 hour. The solution was made to alkaline (pH=9) with 6 M NaOH aqueous solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1) to give {1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}methanol (4.6 g).

후처리

  1. temperaturecooling
  2. temperatureAfter cooling with an ice-bath
  3. stirringstirred at room temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-d1dec7b41ef346e9a6798f4ddf9e3781
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455511B2

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