Ammonium → HCID 68181869, compound

HRID 1398711Notes

Reaction equation

HRID 1398711 reaction equation
[Br:1][C:2]1[C:3]([F:19])=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11](Cl)[N:10]=2)[CH:7]=1.[OH-].[NH4+:21].[NH4+]>CC(O)C>[Br:1][C:2]1[C:3]([F:19])=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:21])[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 223AmmoniumHCID 14923Ammonium HydroxideHCID 86669618HCID 86669618, compound

Product 1

HCID 68181869HCID 68181869, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-(5-bromo-4-fluoro-2-nitrophenyl)-2-chloropyrimidin-4-amine (1.05 g, 3.02 mmol) in 2-propanol (12 mL) in a pressure vessel was added ammonium hydroxide (12 mL, 303 mmol) carefully at RT. The reaction vessel was sealed and stirred at 90° C. for 15 hr (4 bar). Extra aqueous ammonium (4 mL, 100 mmol) was added and the reaction heated at 90° C. for 1 hr then cooled to 0° C. The resultant orange precipitate was filtered and dried by suction filtration to afford the title compound as an orange solid (713 mg, 63% yield); 1H NMR (500 MHz, DMSO) delta 9.55 (s, 1H), 8.44 (d, J=6.6 Hz, 1H), 8.17 (d, J=8.6 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 6.31 (s, 2H), 6.19 (d, J=5.6 Hz, 1H); LC-MS: m/z+329.80 (M+H)+.

Workup

  1. customThe reaction vessel was sealed
  2. temperaturethe reaction heated at 90° C. for 1 hr
  3. temperaturethen cooled to 0° C
  4. filtrationThe resultant orange precipitate was filtered
  5. customdried by suction filtration

Sources & evidence

ORD record
ord-5d1097f9520a4e3d90b819b8a3daa6db
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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