(s)-1-(Tert-butyldimethylsilyloxy)propan-2-amine → 7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 82138

反応式

HRID 82138 の反応式
[Si:1]([O:8][CH2:9][C@@H:10]([NH2:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:13][C:14]1[C:19]([CH2:20][CH:21]=O)=[C:18](Cl)[N:17]=[CH:16][N:15]=1>C(O)C>[Si:1]([O:8][CH2:9][C@@H:10]([N:12]1[C:18]2[N:17]=[CH:16][N:15]=[C:14]([Cl:13])[C:19]=2[CH:20]=[CH:21]1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 10954330(s)-1-(Tert-butyldimethylsilyloxy)propan-2-amineHCID 13989292(4,6-Dichloropyrimidin-5-yl)acetaldehyde

生成物 1

HCID 866720787-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine収率 67%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

(S)-2-tert-Butyldimethylsilyloxy-1-methylethylamine (120 g, 636 mmol) was added to (4,6-dichloropyrimidin-5-yl)acetaldehyde (52.8 g, 276 mmol) in ethanol (500 mL). The mixture was heated to reflux for 45 minutes. The reaction mixture was evaporated in vacuo then the residue was diluted with water (400 mL) and extracted with ethyl acetate (600 mL). The organic extract was evaporated in vacuo and the crude material was purified by column chromatography on silica gel (gradient of pentane:EtOAc 90:10 to 80:20) to afford the title compound as a yellow liquid in 67% yield, 60.4 g.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 45 minutes
  3. customThe reaction mixture was evaporated in vacuo
  4. additionthe residue was diluted with water (400 mL)
  5. extractionextracted with ethyl acetate (600 mL)
  6. extractionThe organic extract
  7. customwas evaporated in vacuo
  8. customthe crude material was purified by column chromatography on silica gel (gradient of pentane:EtOAc 90:10 to 80:20)

出典と根拠

ORDレコード
ord-67d6c939d9664c8db947b75cb61e38c4
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

関連ノート

読み込み中…