Water → 6-(Bromomethyl)thieno[3,2-b]pyrazine

HRID 1184860Notes

Reaction equation

HRID 1184860 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([CH2:10]O)=[CH:9][C:2]=12.P(Br)(Br)[Br:13].O.[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Br:13][CH2:10][C:8]1[S:7][C:3]2[C:2](=[N:1][CH:6]=[CH:5][N:4]=2)[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 67125540Thieno[2,3-b]pyrazin-6-ylmethanol

Product 1

HCID 671255506-(Bromomethyl)thieno[3,2-b]pyrazineYield 63.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of thieno[3,2-b]pyrazin-6-ylmethanol 87 (408 mg, 2.455 mmol) in CH2Cl2 (8 mL) and THF (8 mL) was added phosphorus tribromide (1/166 mL, 12.27 mmol) and stirred overnight at rt. Water was added, alkalized with 2N NaOH and extracted with EtOAc. Organic layer was washed with NaHCO3 (aq) solution, brine, dried and evaporated. Purification by chromatography (CH2CL2) gave pure 6-(bromomethyl)thieno[3,2-b]pyrazine 47 (356 mg, 63%). NMR (400 MHz, CDCl3) 4.80 (s, 2H), 7.71 (s, 1H), 8.49 (d, J=2.3 Hz, 1H), 8.64 (d, J=2.3 Hz, 1H). (m/z)=229 and 231 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washOrganic layer was washed with NaHCO3 (aq) solution, brine
  3. customdried
  4. customevaporated
  5. customPurification by chromatography (CH2CL2)

Sources & evidence

ORD record
ord-41b48f1c844b4fc88f92fdcaca56d5da
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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