Methyl iodide → 3-(7-bromo-1,5-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

HRID 60351Notes

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]([Br:18])[C:11]=2[N:10]([CH3:30])[C:9]1=[O:31])(=[O:3])[CH3:2].CI.[C:34]([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]([CH3:34])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:27])[F:28])[CH:20]=3)=[C:17]([Br: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-(7-bromo-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (See Compound 36, Step 1, 25 mg, 0.050 mmol) in DMF (1 mL) was added CH3I (14.1 mg, 0.10 mmol) followed by K2CO3 (20.6 mg, 0.15 mmol). The reaction was heated at 85° C. for 1.5 h, cooled to RT then diluted with EA (10 mL) and brine (5 mL). The organic layer was washed with aq. 1N LiCl (3×20 mL), dried over Na2SO4 and concentrated to give 3-(7-bromo-1,5-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (25 mg, 97.3% yield) as an oil. LCMS: MH+ 518 and TR=1.877 min. Used without further purification.

Workup

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

Sources & evidence

ORD record: ord-45e5b93c0ec84d9f9242a65eef006f1f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440983B2

Reaction notes

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