Sodium Thiosulfate → 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

HRID 1036588Notes

Reaction equation

HRID 1036588 reaction equation
[I:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19]2[NH:22][C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH2:31])[N:26]=3)=[CH:24][C:18]=2[C:17]1=[O:32])=[O:15])([CH3:12])([CH3:11])[CH3:10].[Al].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19]2[NH:22][C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH2:31])[N:26]=3)=[C:24]([I:1])[C:18]=2[C:17]1=[O:32])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 5359268AluminumHCID 247769152-(2-Amino-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 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 esterYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-iodo succinimide (0.75 g, 3.34 mml) was added to a solution of 2-(2-amino-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester [(1), Q=Boc] (1.0 g, 3.03 mmol) in dry DMF (15 mL) and the reaction mixture was stirred at room temperature overnight, in a flask surrounded by an aluminium sheet. After reaction completion, a solution of Na2S2O3 (10%, 0.100 ml) was added and the product was extracted with DCM (3×0.100 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure to yield the crude 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 as a yellow solid (1.240 g, 2.72 mmol, 90%).

Workup

  1. customAfter reaction completion
  2. extractionthe product was extracted with DCM (3×0.100 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7cbad1df20ba4e26af942d051b2145ed
Source dataset
uspto-grants-2013_10
Patent number
US08546413B2

Reaction notes

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