Potassium Carbonate → HCID 57597142, compound

HRID 1786877Notes

Reaction equation

HRID 1786877 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]2[C:20]3[NH:27][CH:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][C:36]1[CH:37]=[C:38]([S:44](Cl)(=[O:46])=[O:45])[CH:39]=[CH:40][C:41]=1[O:42][CH3:43]>CN(C)C=O.C(OCC)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]2[C:20]3[N:27]([S:44]([C:38]4[CH:39]=[CH:40][C:41]([O:42][CH3:43])=[C:36]([O:35][CH3:34])[CH:37]=4)(=[O:46])=[O:45])[CH:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 67520370HCID 67520370, compound

Product 1

HCID 57597142HCID 57597142, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine hydrochloride (150 mg) was dissolved in N,N-dimethylformamide (1.5 mL), and potassium carbonate (102 mg) and (3,4-dimethoxyphenyl)sulfonyl chloride (96.9 mg) were sequentially added under ice-cooling. The mixture was stirred under ice-cooling for 2 hrs, and at room temperature for 1 hr. The mixture was diluted with ethyl acetate (50 mL) and washed twice with water (30 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100) to give the title compound (95 mg) as a powder.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hrs
  3. washwashed twice with water (30 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100)

Sources & evidence

ORD record
ord-381c2a8b9ebc472ebe4185d0e3002404
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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