Dimethylformamide → HCID 57182539, compound

HRID 1276062Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]2[CH:20]=[CH:21][N:22]=[C:10]12.CN([CH:26]=[O:27])C.[C:28](=[O:31])([O-])[O-].[K+].[K+].Cl[CH2:35][C:36]1[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][C:37]=1[O:38][CH:39](C)[C:40](OC)=O>O>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:35][C:36]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][C:37]=2[O:38][CH2:39][CH2:40][C:28]([O:27][CH3:26])=[O:31])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:17])([F:19])[F:18])[N:11]2[CH:20]=[CH:21][N:22]=[C:10]12

Participants

Conditions

Temperature: 75 °C

Procedure

8-(2-Fluoro-4-hydroxyphenyl)-7,8-dihydro-5-trifluoromethylimidazo[1,2-a]pyrimidin-7-one (200 mg) was dissolved into DMF (6 ml), which was then added with potassium carbonate (106 mg) and methyl 2-(2-(chloromethyl)-5-methylphenoxy)propanoate (155 mg), and stirred for 2 hours at 75° C. Subsequently, the mixture was added with water and extracted with diethyl ether. The organic layer was dried on magnesium sulfate followed by distilling off the solvent under reduced pressure. The thus obtained residue was purified by a preparative thin-layer plate of silica gel (developing solvent: ethyl acetate/hexane=2/3) to give the compound of interest (170 mg).

Workup

extractionextracted with diethyl ether
customThe organic layer was dried on magnesium sulfate
distillationby distilling off the solvent under reduced pressure
customThe thus obtained residue was purified by a preparative thin-layer plate of silica gel (developing solvent: ethyl acetate/hexane=2/3)
customto give the compound of interest (170 mg)

Sources & evidence

ORD record: ord-05089a1ee61241c2b668ed160e963aa7
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06165942

Reaction notes

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