Potassium Carbonate → 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63927Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[NH:11][C:10]=3[O:9][C:8]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].ClCC([Si](C)(C)C)[CH2:36][O:37][CH2:38][CH:39]([Si:42]([CH3:45])([CH3:44])[CH3:43])CCl>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])[NH:13][C:12](=[O:17])[N:11]([CH2:36][O:37][CH2:38][CH2:39][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:10]=3[O:9][C:8]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 5-(4-chlorobenzyl)-6-(3-chlorophenyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (38.7 mg, 0.1 mmol) and K2CO3 (13.8 mg, 0.1 mmol) in DMF (1 mL) at 0° C. was added chloromethyl-2-trimethylsilylethyl ether (33.4 mg, 0.2 mmol). The reaction was stirred at 0° C. for 1 h 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 chromatography eluted with PE/EA (5:1) to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (31 mg, 60.7% yield) as a colorless oil. LCMS: MH+ 517 and TR=2.196 min.

Workup

washThe organic layer was washed with brine (3 mL)
dry with materialdried over Na2SO4
concentrationconcentrated to a residue which
customwas purified by chromatography
washeluted with PE/EA (5:1)

Sources & evidence

ORD record: ord-02589e9c7a11483f9e363d2e088ebb77
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447114B2

Reaction notes

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