Ethyl orthoformate → HCID 117771578, compound

HRID 2201568Notes

Reaction equation

HRID 2201568 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1.[CH2:19](OC(OCC)OCC)C>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:19][N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:9](=[O:10])[C:3]=2[N:4]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 117771064HCID 117771064, compound

Product 1

HCID 117771578HCID 117771578, compoundYield 45%

Conditions

Temperature
130 °C

Procedure

A mixture of 3-amino-6-bromo-N-(2-fluorophenyl)picolinamide (160 mg, 0.516 mmol) in triethoxymethane (5 mL) was stirred at 130° C. for 15 h. The mixture was cooled to room temperature and extracted with ethyl acetate (10 mL*3), the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 6-bromo-3-(2-fluorophenyl)pyrido[3,2-d]pyrimidin-4(3H)-one (75 mg, yield: 45%), which was used for the next step without further purification. MS (M+H)+:320/322

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (10 mL*3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-501e833da7d24dbf9cab3ba41977885b
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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