Water → HCID 117818873, compound

HRID 1753247Notes

Reaction equation

HRID 1753247 reaction equation
[N+:1]([C:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[NH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:20][C:21]1[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[N:24]=[CH:23][N:22]=1.O>CN(C=O)C>[CH3:29][O:28][C:25]1[N:24]=[CH:23][N:22]=[C:21]([CH2:20][N:6]2[C:7]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5]2)[C:26]=1[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 576136403-Nitro-1H-pyrrolo[3,2-b]pyridineHCID 734250974-(Chloromethyl)-6-methoxy-5-methylpyrimidine

Product 1

HCID 117818873HCID 117818873, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 3-Nitro-1H-pyrrolo[3,2-b]pyridine (25b) (0.5 g, 3.04 mmol) and K2CO3 (0.5 g, 9.12 mmol) in DMF (10 mL) was added 4-(chloromethyl)-6-methoxy-5-methylpyrimidine (0.7 g, 6.09 mmol) and the resulting mixture was stirred for 16 h at room temperature. Then the reaction mixture was poured in to water (50 mL) and extracted with dichloromethane (2×50 mL). The combined organic layer was washed with brine and the solvent was evaporated under reduced pressure to yield 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-3-nitro-1H-pyrrolo[3,2-b]pyridine (25c) [300 mg (33%)] as a pale yellow solid.

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. washThe combined organic layer was washed with brine
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-376ca9cdce474da3a1659c1939a8a31b
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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