Imidazole → HCID 58507769, compound

HRID 1408462Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)[N:12]=2)[CH2:3][CH2:2]1.N1C=CN=C1.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>CN(C=O)C>[Si:32]([O:19][C:15]1[CH:14]=[C:13]([C:11]2[N:12]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=2)[CH:18]=[CH:17][CH:16]=1)([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 70 °C

Procedure

3-(4-morpholinothieno[3,2-d]pyrimidin-2-yl)phenol [synthesized according to Hayakawa et al., Bioorganic & Med. Chem. 14:6847-6858 (2006)] (540 mg, 1.72 mmol, 1.0 eq.) was dissolved in DMF (5 ml). To this imidazole (936 mg, 13.8 mmol, 8.0 eq.) and TBDMSCl (909 mg, 6.02 mmol, 3.5 eq.) were added and the mixture was heated at 70° C. for 3 h. DMF was evaporated under reduced pressure and purification by flash chromatography (hexane:ethyl acetate, gradient from 100%-50% hexane in EtOAc) yielded the title compound as a white solid.

Workup

customDMF was evaporated under reduced pressure and purification by flash chromatography (hexane:ethyl acetate, gradient from 100%-50% hexane in EtOAc)

Sources & evidence

ORD record: ord-5b408368b72c4ed1b5dbe00273071794
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921361B2

Reaction notes

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