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

Potassium Carbonate → (6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]carbamic acid tert-butyl ester

HRID 1692855
Notes
Print preview

Reaction equation

HRID 1692855 reaction equation
[C:1]([O:5][C:6](=[O:34])[N:7]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([OH:33])[C:24]2[C:32]3[CH:31]=[N:30][CH:29]=[N:28][C:27]=3[NH:26][CH:25]=2)=[CH:19][N:18]=1)[CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:24]2[C:32]3[CH:31]=[N:30][CH:29]=[N:28][C:27]=3[NH:26][CH:25]=2)=[O:33])=[CH:19][N:18]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 57963192{5-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 57963060(6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]carbamic acid tert-butyl esterYield 35%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To {5-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (72, 0.189 g, 0.409 mmol) in 4.0 mL of dichloromethane, Dess-Martin periodinane (0.208 g, 0.490 mmol) was added. The reaction was stirred at room temperature for 1 hour, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with methanol and dichloromethane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (73, 66 mg). 1H NMR was consistent with the compound structure.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with methanol and dichloromethane
  7. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-2cf18d440b4f4f0ab2b7848d4bbc195c
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158636B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes