1-Chloro-4-(chloromethyl)benzene → HCID 118863777, compound

HRID 60356Notes

Reaction equation

HRID 60356 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[NH:15][CH:16]=[CH:17][C:11]=2[N:10]([CH3:18])[C:9]1=[O:19])(=[O:3])[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(=O)OCC.O>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:27][C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=3)[CH:16]=[CH:17][C:11]=2[N:10]([CH3:18])[C:9]1=[O:19])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 1188637843-(1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

Product 1

HCID 118863777HCID 118863777, compoundYield 60.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-(1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (52 mg, 0.2 mmol) in DMF (3 mL) was added 1-chloro-4-(chloromethyl)benzene (64 mg, 0.4 mmol) and K2CO3 (82 mg, 0.6 mmol). The reaction was heated at 85° C. for 2 h, cooled to RT then diluted with EA (30 mL) and water (20 mL). The organic layer was washed with aq. 1N LiCl solution (3×10 mL), dried over Na2SO4 and concentrated to give 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (47 mg, 59% yield) as a solid. LCMS: MH+ 390 and TR=1.399 min. Used without further purification.

Workup

  1. temperaturecooled to RT
  2. washThe organic layer was washed with aq. 1N LiCl solution (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c547cd6f62144d2daac6f4f5c7f3780a
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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