HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

N-bromobutanimide → 6-bromo-7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 336137
Notes
Print preview

Reaction equation

HRID 336137 reaction equation
[Br:1]N1C(=O)CCC1=O.[Si:9]([O:16][CH:17]([CH:39]=[CH2:40])[CH2:18][N:19]1[C:23]2[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=2[C:21]([C:29]2[CH:30]=[N:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:20]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:20]1[N:19]([CH2:18][CH:17]([O:16][Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])[CH:39]=[CH2:40])[C:23]2[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=2[C:21]=1[C:29]1[CH:30]=[N:31][C:32]2[C:37]([CH:38]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 867112787-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 867112776-bromo-7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

N-Bromosuccinimide (894 mg) was added to a solution of 7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (2.13 g) obtained in Step 5 in DMF (25 ml) at room temperature. After stirring at the same temperature for 30 minutes, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a yellow solid (2.26 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8b20a3e1ec6f4e0c872a46561ffaf299
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889666B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes