Acetic Anhydride → HCID 117771835, compound

HRID 2201576Notes

Reaction equation

HRID 2201576 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[CH3:19]C(OC(C)=O)=O>C(OC(OCC)OCC)C>[Br:8][C:5]1[N:4]=[C:3]2[C:2](=[N:7][CH:6]=1)[N:1]=[CH:19][N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:9]2=[O:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 117771083HCID 117771083, compound

Product 1

HCID 117771835HCID 117771835, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-amino-6-bromo-N-(3-fluorophenyl)pyrazine-2-carboxamide (100 mg, 0.29 mmol) in triethoxymethane (5 mL) was added Ac2O (1 mL). The mixture was stirred at 130° C. for 1 h and 90° C. for 3 h. After being cooled and extracted with EtOAc, the combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by prep-TLC (PE:EtOAc=1:1) to give the pure product of 6-bromo-3-(3-fluorophenyl)pteridin-4(3H)-one (60 mg, yield: 60%). 1H-NMR (CDCl3, 400 MHz) δ 8.98 (s, 1H), 8.35 (s, 1H), 7.49˜7.55 (m, 1H), 7.15˜7.24 (m, 3H). MS (M+H)+: 321/323.

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with EtOAc
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by prep-TLC (PE:EtOAc=1:1)

Sources & evidence

ORD record
ord-aea61acbac4c4ffeaafc7eef65e88e4d
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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