Potassium Carbonate → HCID 10151688, compound

HRID 2181620Notes

Reaction equation

HRID 2181620 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[N:16]=[C:15]([CH2:18][CH3:19])[NH:14][C:13]=2[C:12](=[O:20])[N:11]([CH3:21])[C:10]1=[O:22].C([O-])([O-])=O.[K+].[K+].[CH2:29](Cl)[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOCC>[CH2:31]([O:30][CH2:29][N:14]1[C:13]2[C:12](=[O:20])[N:11]([CH3:21])[C:10](=[O:22])[N:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[C:17]=2[N:16]=[C:15]1[CH2:18][CH3:19])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl etherHCID 516892Sodium BicarbonateHCID 11772127HCID 11772127, compound

Product 1

HCID 10151688HCID 10151688, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione (6.00 g, 17.69 mmol), prepared according to the procedure in example 1, was dissolved in anhydrous DMF (80 mL). K2CO3 (6.11 g, 44.23 mmol), Bu4NI (1.31 g, 3.54 mmol) and BOMCl (4.4 mL, 31.84 mmol) were added and the reaction mixture was heated at 45° C. for 50 min. The reaction mixture was cooled to rt and was stirred with saturated aqueous NaHCO3 (180 mL) for 30 min. The mixture was poured into a separatory funnel containing ether (600 mL). The organic layer was washed with H2O (4×80 mL), brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (40% ethyl acetate in hexanes) to give 7-benzyloxymethyl-3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione (5.28 g, 65% yield) as an amorphous solid: 1H NMR (300 MHz, CDCl3) δ 7.59 (d, J=2.2 Hz, 1H), 7.42 (dd, J=8.4, 2.2 Hz, 1H), 7.37-7.26 (m, 6H), 5.86 (ABq, JAB=11.0, Δυ=39.7 Hz, 2H), 4.72 (s, 2H), 3.46 (s, 3H), 2.79 (q, J=7.7 Hz, 2H), 1.25 (t, J=7.6 Hz, 3H); LRMS (APCI) m/e 459.0 [(M+H)+, calcd for C22H21N4O3Cl2 459.1].

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. additionThe mixture was poured into a separatory funnel
  3. washThe organic layer was washed with H2O (4×80 mL), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4f43af065a8040ce9acccb6125f991ba
Source dataset
uspto-grants-2005_05
Patent number
US06894045B2

Reaction notes

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