Tert-butyl thieno[2,3-b]pyrazin-6-ylcarbamate → Thieno[2,3-b]pyrazin-6-amine
Reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([NH:10]C(=O)OC(C)(C)C)=[CH:9][C:2]=12>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([NH2:10])=[CH:9][C:2]=12Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A red solution of tert-butyl thieno[2,3-b]pyrazin-6-ylcarbamate (5.09 mmol, 1.28 g) in 66% TFA in CH2Cl2 25 mL was stirred overnight at room temperature The reaction mixture was concentrated in vacuo, dissolved in ethyl acetate, washed with NaHCO3 solution, brine, dried and evaporated to give thieno[2,3-b]pyrazin-6-amine 106 (620 mg, 81%). NMR (400 MHz, DMSO-d6) 5.98 (s, 1H), 7.17 (br s, 2H), 7.93 (d, J=2.7 Hz, 1H), 8.20 (d, J=2.7 Hz, 1H).
Workup
- concentrationwas concentrated in vacuo
- dissolutiondissolved in ethyl acetate
- washwashed with NaHCO3 solution, brine
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-a209f3cff04a47af9913001a005bfa9e
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669256B2
Reaction notes
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