Water → HCID 66620899, compound

HRID 415558Notes

Reaction equation

HRID 415558 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:19](S(C)(=O)=O)=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1.O>C1COCC1>[Br:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]3[N:20]4[CH2:21][CH2:22][CH2:23][N:24]([C:25]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:31])[C:19]4=[N:18][C:13]=3[CH:14]=[N:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxide2×HCID 66620252HCID 66620252, compound

Product 1

HCID 66620899HCID 66620899, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, potassium tert-butoxide (6 mL of a 1 M solution in THF) was added to a solution of tert-butyl 3-(7-bromo-2-(methylsulfonyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate (2.3 g, 4.8 mmol) in THF (50 mL). The reaction was stirred overnight at room temperature, and an analysis by LC/MS indicated the presence of starting material. Additional potassium tert-butoxide solution (4 mL) was added, and the reaction was stirred for an additional 30 minutes at room temperature. The reaction was poured into water. A solid was present and was washed with water and dried for three days in a vacuum oven to provide 0.95 g of tert-butyl 3-bromo-10,11-dihydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline-8(9H)-carboxylate.

Workup

  1. stirringthe reaction was stirred for an additional 30 minutes at room temperature
  2. washwas washed with water
  3. customdried for three days in a vacuum oven

Sources & evidence

ORD record
ord-ba8346c4295b4e5b86d9a06668ae9120
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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