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

HRID 1253832ノート

反応式

HRID 1253832 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 59845595HCID 59845595、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d1dec7b41ef346e9a6798f4ddf9e3781
出典データセット
uspto-grants-2013_06
特許番号
US08455511B2

反応ノート

読み込み中…