Ethyl orthoformate → HCID 117771590, compound

HRID 2201565Notes

Reaction equation

HRID 2201565 reaction equation
[NH2:1][C:2]1[N:17]=[CH:16][C:15]([Br:18])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:5].[CH2:19](OC(OCC)OCC)C>>[Br:18][C:15]1[CH:16]=[N:17][C:2]2[N:1]=[CH:19][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[F:13])[C:4](=[O:5])[C:3]=2[CH:14]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 62155572HCID 62155572, compound

Product 1

HCID 117771590HCID 117771590, compoundYield 97%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-amino-5-bromo-N-(2-fluorophenyl)nicotinamide (100 mg, 0.32 mmol) and 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[2,3-d]pyrimidin-4(3H)-one (100 mg, 97% yield), 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-50a6430d839b49f7976da5640c5e0b3e
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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