9-Bromothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine → HCID 68786598, compound

HRID 2098065Notes

Reaction equation

Br[C:2]1[C:6]2[C:7]3[N:8]([N:11]=[CH:12][N:13]=3)[CH:9]=[N:10][C:5]=2[S:4][CH:3]=1.[Cu][C:15]#[N:16]>CN(C=O)C>[N:13]1[CH:12]=[N:11][N:8]2[C:7]=1[C:6]1[C:2]([C:15]#[N:16])=[CH:3][S:4][C:5]=1[N:10]=[CH:9]2

Participants

Conditions

Temperature: 150 °C

Procedure

9-Bromothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (1.16 g, 4.55 mmol) was dissolved in DMF (23 mL), and copper(I) cyanide (817 mg, 9.1 mmol) was added. This mixture was heated to 150° C. for 23 h, whereupon the reaction mixture was concentrated under reduced pressure, and the residue purified by flash chromatography. LCMS method [4], retention time=0.890 min; MS (ESI) 202.0 (MH+); 1H NMR (300 MHz, CDCl3) δ 9.36 (s, 1H), 8.57 (s, 1H), 8.32 (s, 1H).

Workup

concentrationwas concentrated under reduced pressure
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-db6aabb438794ed584b303e69c409ae4
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450363B2

Reaction notes

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