Methyl iodide → HCID 118863144, compound

HRID 63930Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (22.25 mg, 0.05 mmol), K2CO3 (13.8 mg, 0.1 mmol) in DMF (1 mL) was added CH3I (8.5 mg, 0.06 mmol). The reaction was heated in a sealed tube at 65° C. for 2 h, cooled to RT then diluted with EA (10 mL) and water (3 mL). The organic layer was washed with brine (3 mL) dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methylfuro[2,3-d]pyrimidine-2,4(1H,3H)-dione (3 mg, 13% yield) as a white solid. 1H NMR (DMSO-d6) δ: 7.62 (s, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.47 (t, J=7.9 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.35 (d, J=8.5 Hz, 2H), 7.26 (d, J=8.5 Hz, 2H), 4.47 (t, J=5.2 Hz, 1H), 4.32 (s, 2H), 3.97-3.81 (m, 2H), 3.53 (s, 3H), 3.43 (dd, J=11.8, 6.4 Hz, 2H), 1.75-1.60 (m, 2H). LCMS: MH+ 459 and TR=3.047 min.

Workup

temperaturecooled to RT
washThe organic layer was washed with brine (3 mL)
dry with materialdried over Na2SO4
concentrationconcentrated to a residue which
customwas purified by Prep HPLC

Sources & evidence

ORD record: ord-0076ef0a4ffd4f40a05bcec80b165509
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447114B2

Reaction notes

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