Water → HCID 22386559, compound

HRID 1072421Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([S:17][CH2:18][CH3:19])[N:14]3[CH:20]=[CH:21][N:22]=[C:13]3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH:34]([NH:37][CH:38](C)C)(C)[CH3:35].O>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([S:17][C:18]3[CH:35]=[CH:34][N:37]=[CH:38][CH:19]=3)[N:14]3[CH:20]=[CH:21][N:22]=[C:13]3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

7-(3,4-Dimethoxy-phenyl)-5-ethylsulfanyl-imidazo[1,2-c]pyrimidine (335 mg, 1.06 mmol) was dissolved in trifluoroacetic acid (TFA, 5 ml). After 5 min the TFA was evaporated. The residue was dissolved in 10 ml CH2Cl2. The solution was cooled to 0° C. and m-CPBA (70%, 524 mg, 2.12 mmol) was added. The reaction mixture was allowed to warm to room temperature and was stirred for 5 h. Diisopropylamine (598 mg, 4.63 mmol) and thiol (254 mg, 2.28 mmol) were added and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and extraction was carried out with CHCl3. The organic layer was washed with brine, sat. NaHCO3, brine and dried over Na2SO4. The organic layer was then concentrated to give the crude product of 7-(3,4-Dimethoxy-phenyl)-5-(pyridin-4-ylsulfanyl)-imidazo[1,2-c]pyrimidine which was purified by column chromatography (160 mg, 41%).

Workup

customAfter 5 min the TFA was evaporated
dissolutionThe residue was dissolved in 10 ml CH2Cl2
temperatureto warm to room temperature
stirringthe mixture was stirred at room temperature overnight
washThe organic layer was washed with brine, sat. NaHCO3, brine
dry with materialdried over Na2SO4
concentrationThe organic layer was then concentrated

Sources & evidence

ORD record: ord-82a2d923d73b444f8fab364227d66053
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911443B2

Reaction notes

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