1-Chloro-4-(chloromethyl)benzene → HCID 118863785, compound

HRID 60344Notes

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:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[C:17]([CH3:18])[C:11]=2[N:10]([CH3:30])[C:9]1=[O:31])(=[O:3])[CH3:2].[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Cl)=[CH:35][CH:34]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(=O)OCC.[Cl-].[Na+].O>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:39][C:36]3[CH:37]=[CH:38][C:33]([Cl:32])=[CH:34][CH:35]=3)[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:27])([F:28])[F:29])[CH:20]=3)=[C:17]([CH3:18])[C:11]=2[N:10]([CH3:30])[C:9]1=[O:31])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 3-(1,7-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (See Compound 36, Step 2, 140 mg, 0.319 mmol) in DMF (2 mL) was added 1-chloro-4-(chloromethyl)benzene (102.6 mg, 0.637 mmol) followed by K2CO3 (132.1 mg, 0.956 mmol). The reaction was heated at 85° C. for 2 h, cooled to RT then diluted with EA (10 mL) and brine (5 mL). The organic layer was washed with aqueous 1N LiCl (3×20 mL), dried over Na2SO4 and concentrated to give 3-(5-(4-chlorobenzyl)-1,7-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (120 mg, 66.7% yield) LCMS: MH+ 564 and TR=2.151 min. Used without further purification.

Workup

temperaturecooled to RT
washThe organic layer was washed with aqueous 1N LiCl (3×20 mL)
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-a39f72fa6c9a415ebbb1e0e4e3135ff3
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440983B2

Reaction notes

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