Potassium Carbonate → 7-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-one

HRID 860088Notes

Reaction equation

HRID 860088 reaction equation
COP([CH2:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:18]=[C:17]2[NH:19][CH2:20][CH2:21][C:16]2=[CH:15][CH:14]=1)(=O)OC.[CH3:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][N:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH:19]1[C:17]2=[N:18][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[O:22])[CH:7]=[CH:30][C:27]3[CH:26]=[N:25][C:24]([CH3:23])=[N:29][CH:28]=3)=[CH:14][CH:15]=[C:16]2[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 20622453[6-(2,3-Dihydro-1H-pyrrolo [2,3-b]pyridin-6-yl)-2-oxo-hexyl]-phosphonic acid dimethyl ester

Product 1

HCID 696668007-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-oneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 23-7 (0.49 g, 1.5 mmol) and 2-methyl-pyrimidine-5-carbaldehyde (0.183 g, 1.5 mmol) in 15 mL DMF was added K2CO3 (0.310 g, 2.25 mmol). The mixture was stirred at ambient temperature for 2 hr and concentrated to a paste. The residue was purified by PCTLC (0–10% MeOH/CH2Cl2) which provided 0.400 g (83% yield) of 23-8.

Workup

  1. concentrationconcentrated to a paste
  2. customThe residue was purified by PCTLC (0–10% MeOH/CH2Cl2) which

Sources & evidence

ORD record
ord-20e915d9ed0b4d939ef3e7dce14c8161
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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