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

HRID 869332
Notes
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Reaction equation

HRID 869332 reaction equation
[I-:1].[Cs+].II.N(OCCCCC)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23]2[N:26](C)[C:27]([C:29]3[CH:34]=[CH:33][N:32]=[C:31](N)[N:30]=3)=[CH:28][C:22]=2[C:21]1=[O:37])=[O:19])([CH3:16])([CH3:15])[CH3:14]>COCCOC.[Cu](I)I.C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23]2[NH:26][C:27]([C:29]3[CH:34]=[CH:33][N:32]=[C:31]([I:1])[N:30]=3)=[CH:28][C:22]=2[C:21]1=[O:37])=[O:19])([CH3:16])([CH3:15])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 807IodineHCID 10026Pentyl nitriteHCID 24601Cesium iodideHCID 247765532-(2-Amino-pyrimidin-4-yl)-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 866678782-(2-Iodo-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl esterYield 16.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Cesium iodide (1.29 g, 4.97 mmol), iodine (0.63 g, 2.48 mmol), copper iodide (0.283 g, 1.48 mmol) and amyl nitrite (0.87 g, 7.45 mmol) were added under argon to a solution of 2-(2-amino-pyrimidin-4-yl)-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]-pyridine-5-carboxylic acid tert-butyl ester (synthesised as reported in Example 9) (1.137 g, 3.30 mmol) in DME (30.0 ml). The reaction mixture was stirred at 80° C. for 4 h. DCM was added to the solution (20 ml) and the organic layer was washed with a saturated solution of NaHCO3 (1×30 ml), with a saturated solution of Na2S2O3 (1×30 ml), with purite water (1×30 ml) and it was dried over Na2SO4. The filtrate was purified by flash chromatography, over silica gel, using DCM/MeOH (9.8:0.2) as eluent, to afford 2-(2-iodo-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.240 g, 0.53 mmol, 16%) as a yellow solid.

Workup

  1. washthe organic layer was washed with a saturated solution of NaHCO3 (1×30 ml), with a saturated solution of Na2S2O3 (1×30 ml), with purite water (1×30 ml) and it
  2. dry with materialwas dried over Na2SO4
  3. customThe filtrate was purified by flash chromatography, over silica gel

Sources & evidence

ORD record
ord-fef57c0ae2b84c0c99a97bb40a554829
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969366B2

Reaction notes

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