Potassium Carbonate → HCID 57597260, compound

HRID 1786853Notes

Reaction equation

HRID 1786853 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]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[C:39](Cl)=[O:40]>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]2[C:20]3[N:27]([C:39](=[O:40])[C:38]4[CH:42]=[CH:43][C:44]([O:45][CH3:46])=[C:36]([O:35][CH3:34])[CH:37]=4)[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77070Veratroyl chlorideHCID 67520370HCID 67520370, compound

Product 1

HCID 57597260HCID 57597260, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, to a suspension of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine hydrochloride (150 mg) and potassium carbonate (102 mg) in N,N-dimethylformamide (1.5 mL) was added 3,4-dimethoxybenzoyl chloride (82 mg), and the mixture was stirred under ice-cooling, for 1 hr. The mixture was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was washed with saturated brine (30 mL), 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→ethyl acetate:methanol=80:20), and crystallized from diisopropyl ether to give the title compound (104 mg).

Workup

  1. temperaturecooling, for 1 hr
  2. customThe mixture was partitioned between ethyl acetate (50 mL) and water (30 mL)
  3. washThe organic layer was washed with saturated brine (30 mL)
  4. dry with materialdried 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→ethyl acetate:methanol=80:20)
  8. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-f5c0dd2c63a3498bb2f7c23fcfcac790
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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