Water → 2-(2-Amino-pyrimidin-4-yl)-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 1036589Notes

Reaction equation

HRID 1036589 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]2[NH:20][C:21]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[N:25]=3)=[C:22]([I:23])[C:16]=2[C:15]1=[O:31])=[O:13])([CH3:10])([CH3:9])[CH3:8].CI.O>CN(C=O)C.C(Cl)Cl>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]2[N:20]([CH3:1])[C:21]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[N:25]=3)=[C:22]([I:23])[C:16]=2[C:15]1=[O:31])=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 672844762-(2-Amino-pyrimidin-4-yl)-3-iodo-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 672843262-(2-Amino-pyrimidin-4-yl)-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Cesium carbonate (2.17 g, 6.68 mmol) was added to a solution of 2-(2-amino-pyrimidin-4-yl)-3-iodo-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (1.38 g, 3.03 mmol) in DMF (60 mL) and the mixture was stirred at room temperature for 1 h. Methyl iodide (0.948 g, 6.68 mmol) was then added and after 2 h stirring at room temperature, water (0.100 mL) and DCM (0.100 mL) were poured into the reaction vessel. The organic layer was separated, dried over Na2SO4, and concentrated under vacuum to yield the crude 2-(2-amino-pyrimidin-4-yl)-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester as a brown solid (0.854 g, 1.8 mmol, 60%).

Workup

  1. stirringstirring at room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-638d951d6d2544d7ab1d3193661b5cbb
Source dataset
uspto-grants-2013_10
Patent number
US08546413B2

Reaction notes

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