Sodium Iodide → HCID 58774598, compound
Reaction equation
Br[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][C:7]2[C:10]3[C:15]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:24][C:6]=2[CH2:5]1.[I-].[Na+].[CH3:27][O-:28].[Na+]>CN(C=O)C>[Br:23][C:19]1[CH:18]=[C:17]([NH:16][C:15]2[C:10]3[C:7]4[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][O:28][CH3:27])[CH2:5][C:6]=4[S:24][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:22]=[CH:21][CH:20]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of DMF were added 52 mg (0.11 mmol, 1 equiv) of N-[7-(2-bromoethyl)5,6,7,8tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl]-N-(3-bromophenyl)amine, 17 mg (0.11 mmol, 1 equiv) sodium iodide, and 18 mg (0.33 mmol, 3 equiv) sodium methoxide. The solution was heated at 80° C. for 2 h and upon cooling the solution was purified by prep HPLC (10–90% ACN-H2O). The resulting pure fractions were made basic in aqueous saturated sodium bicarbonate and extracted into EtOAc (10 mL). The EtOAc layer was washed with water (1×10 mL) and dried over MgSO4. The solution was evaporated under reduced pressure yielding 20 mg (44%) of desired product, 90, as a white solid. 1H-NMR (CDCl3-d) δ 8.52 (s, 1H), 7.94 (m, 1H), 7.59 (m, 1H), 7.24 (m, 2H), 7.13 (s, 1H), 3.55 (t, 2H), 3.39 (s, 3H), 3.12 (m, 2H), 3.01 (m, 1H), 2.56 (m, 1H), 2.13 (m, 2H), 1.74 (m, 3H); TLC Rf=0.75 (9:1 CH2Cl2/MeOH); LCMS RT=3.57 min; [M+H]+=418.2.
Workup
- temperatureupon cooling the solution
- customwas purified by prep HPLC (10–90% ACN-H2O)
- extractionextracted into EtOAc (10 mL)
- washThe EtOAc layer was washed with water (1×10 mL)
- dry with materialdried over MgSO4
- customThe solution was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-70fc8f12bdaa4f6f972dd7924411523a
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238701B2
Reaction notes
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