Tert-butyl thieno[2,3-b]pyrazin-6-ylcarbamate → Thieno[2,3-b]pyrazin-6-amine

HRID 1184922Notes

Reaction equation

HRID 1184922 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]=12

Participants

4

Reactant 1

HCID 58873972Tert-butyl thieno[2,3-b]pyrazin-6-ylcarbamate

Product 1

HCID 58874087Thieno[2,3-b]pyrazin-6-amineYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

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

  1. concentrationwas concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with NaHCO3 solution, brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-a209f3cff04a47af9913001a005bfa9e
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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