Water → 3-(3-Amino-benzyl)-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

HRID 869324Notes

Reaction equation

HRID 869324 reaction equation
[Cl-].[NH4+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH3:36])[C:17]([C:29]3[CH:34]=[CH:33][N:32]=[C:31]([NH2:35])[N:30]=3)=[C:18]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)[C:12]=2[C:11]1=[O:37])=[O:9])([CH3:6])([CH3:5])[CH3:4].O>O1CCOCC1.[Zn]>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH3:36])[C:17]([C:29]3[CH:34]=[CH:33][N:32]=[C:31]([NH2:35])[N:30]=3)=[C:18]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=3)[C:12]=2[C:11]1=[O:37])=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67285760HCID 67285760, compound

Product 1

HCID 672845333-(3-Amino-benzyl)-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 esterYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

Zn (0.041 g, 0.632 mmol) and ammonium chloride (0.034 g, 1.58 mmol) were added to a solution of 2-(2-Amino-pyrimidin-4-yl)-1-methyl-3-(3-nitro-benzyl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.075 g, 0.158 mmol) was dissolved in dioxane (5 ml) and purite water (1.0 ml) and the reaction mixture was stirred at 75° C. for 2 hours. A solution of Na2HPO4 (10 ml) was then added and the water layer was extracted with EtOAc (3×10 ml). The organic layers were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure yielding 3-(3-Amino-benzyl)-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 (0.071 g, 0.158 mmol, 100%).

Workup

  1. extractionthe water layer was extracted with EtOAc (3×10 ml)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-588deeb980974adcaea54bb68cd130e0
Source dataset
uspto-grants-2015_03
Patent number
US08969366B2

Reaction notes

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