Bromine → 7-Bromothieno[3,2-d]pyrimidine
Reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[CH:4]=[N:3][CH:2]=1.C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C>[Br:15][C:7]1[C:6]2[N:1]=[CH:2][N:3]=[CH:4][C:5]=2[S:9][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Thieno[3,2-d]pyrimidine (0.163 g, 1.20 mmol) was dissolved in acetic acid (3 mL). Sodium acetate (0.196 g, 2.39 mmol) was added while stirring, followed by bromine (0.38 g, 2.4 mmol). The reaction mixture was heated in a microwave reactor at 90° C. for 90 min. Solvent was removed by rotary evaporation, then under high vacuum. Purification by ISCO chromatography (0 to 10% methanol:DCM) afforded 0.152 g (59%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 9.36 (s, 1 H), 9.30 (s, 1 H), 8.05 (s, 1 H); MS (ESI): 214.97, 216.99 [M+H]+.
Workup
- customSolvent was removed by rotary evaporation
- customPurification by ISCO chromatography (0 to 10% methanol:DCM)
Sources & evidence
- ORD record
- ord-b4889238c68949189b5f4b1a0612511b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378104B2
Reaction notes
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