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Ammonia → 4-Amino-6-chloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamide

HRID 1052438
Notes
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Reaction equation

HRID 1052438 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([F:19])[CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:21]>O1CCOCC1>[NH2:21][C:6]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([F:19])[CH:12]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1184337684,6-Dichloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamide

Product 1

HCID 901026694-Amino-6-chloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

4,6-Dichloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamide (720 mg, 2.28 mmol) was dissolved in dioxane (10 ml) and cooled in an ice bath. Ammonia solution (1.63 mL, 7N in MeOH) was added dropwise and the mixture was stirred at 0° C. for 6 h and overnight at room temperature. After evaporation of the solvent under reduced pressure, the residue (675 mg, 100%) was used in the next synthetic step without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customAfter evaporation of the solvent under reduced pressure
  3. customthe residue (675 mg, 100%) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-90d8c73a239246a0aa53c947fda08dd8
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09388189B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes