Ammonium Hydroxide → N-(2-amino-6-chloro-4-pyrimidinyl)-N-[3-fluoro-4-(4-pyridinylsulfanyl)phenyl]amine

HRID 496019Notes

Reaction equation

HRID 496019 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[S:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[NH2:14].[OH-].[NH4+]>O.Cl>[NH2:1][C:2]1[N:3]=[C:4]([NH:14][C:13]2[CH:15]=[CH:16][C:17]([S:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:11]([F:10])[CH:12]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 70592743-Fluoro-4-(4-pyridinylsulfanyl)aniline

Product 1

HCID 22324284N-(2-amino-6-chloro-4-pyrimidinyl)-N-[3-fluoro-4-(4-pyridinylsulfanyl)phenyl]amineYield 47.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-4,6 dichloropyrimidine (A21, 12 mmol) and 3-fluoro-4-(4-pyridinylthio)-aniline (B7,12 mmol) were suspended in water (150 mL) and treated with 10 drops of concentrated hydrochloric acid. The mixture was stirred at 100° C. overnight. The clear solution was then neutralized with ammonium hydroxide. The precipitated yellow product was filtered, washed with water, and purified by column chromatography with 1-3% MeOH in CH2Cl2 to give the desired product as a white solid (1.98 g, 47%).

Workup

  1. filtrationThe precipitated yellow product was filtered
  2. washwashed with water
  3. custompurified by column chromatography with 1-3% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-75b5f6d320e5437e882924ed062ada56
Source dataset
uspto-grants-2005_09
Patent number
US06943172B2

Reaction notes

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