1-Chloro-4-(chloromethyl)benzene → HCID 118863766, compound

HRID 60348Notes

Reaction equation

HRID 60348 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[CH:17][C:11]=2[N:10]([CH3:25])[C:9]1=[O:26])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40]Cl)=[CH:36][CH:35]=1>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]([CH2:40][C:37]3[CH:38]=[CH:39][C:34]([Cl:33])=[CH:35][CH:36]=3)[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[CH:17][C:11]=2[N:10]([CH3:25])[C:9]1=[O:26])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 1188637723-(6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propylacetate

Product 1

HCID 118863766HCID 118863766, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 3-(6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (60 mg, 0.16 mmol), K2CO3 (110 mg, 0.80 mmol) in DMF (2 ml) was added 1-chloro-4-(chloromethyl)benzene (51 mg, 0.32 mmol). The reaction was heated at 85° C. for 2 h, cooled to RT then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-(5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (40 mg, 50% yield) as an oil. LCMS: MH+ 500 and TR=1.847 min. Used without further purification.

Workup

  1. temperaturecooled to RT
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cfae0f83fee3441ea6a33907f0460a15
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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