(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

Reaction equation

HRID 82138 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-67d6c939d9664c8db947b75cb61e38c4
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

Loading…