Potassium Carbonate → HCID 86643465, compound

HRID 1422490Notes

Reaction equation

HRID 1422490 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([Cl:11])[N:3]=1.Br[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 516892Sodium BicarbonateHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 86643465HCID 86643465, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,6-dichloro-9H-purine (5.0 g, 26.5 mmol), methyl 2-bromopropanoate (5.3 g, 31.7 mmol) and potassium carbonate (11.0 g, 79.4 mmol) in anhydrous DMF (100 mL) was heated at 100° C. for 15 h. Sat. aqueous sodium bicarbonate solution was added and reaction was extracted with ethyl acetate (150 ml×3). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (10 to 80% ethyl acetate in hexane eluant) to afford the title compound as a white solid. MS m/z 275.0 (M+1).

Workup

  1. customreaction
  2. extractionwas extracted with ethyl acetate (150 ml×3)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (10 to 80% ethyl acetate in hexane eluant)

Sources & evidence

ORD record
ord-47f5ee2277244f5591423123706523b1
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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