Sodium borohydride → Thieno[2,3-b]pyrazin-6-ylmethanol

HRID 1184859Notes

Reaction equation

HRID 1184859 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([C:10](OCC)=[O:11])=[CH:9][C:2]=12.[BH4-].[Na+]>C1COCC1.CO.[NH4+].[Cl-]>[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([CH2:10][OH:11])=[CH:9][C:2]=12

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 12299125Ethyl thieno[2,3-b]pyrazine-6-carboxylate

Product 1

HCID 67125540Thieno[2,3-b]pyrazin-6-ylmethanolYield 91.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of ethyl thieno[3,2-b]pyrazine-6-carboxylate 86 (600 mg, 2.88 mmol) in THF (3 mL) and methanol (3 mL) was added sodium borohydride (1.09 g, 28.8 mmol). The reaction was stirred at rt for 30 min. Poured in NH4Cl solution and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated to give the crude thieno[3,2-b]pyrazin-6-ylmethanol 87 (438 mg, 91%) which was used without further purification.

Workup

  1. extractionextracted with EtOAc
  2. washOrganic layer was washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-1e7969c25aee441cad9518918c62efb9
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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