N-methyl-2-pyrrolidone → HCID 10180571, compound

HRID 2414767Notes

Reaction equation

HRID 2414767 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([NH2:17])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:18])[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:23]=[C:22]([NH2:33])[N:21]=1.CN1CCCC1=O>Cl.[OH-].[Na+]>[NH2:33][C:22]1[N:21]=[C:20]([NH:18][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:16]=[C:15]3[NH2:17])[CH:25]=[C:24]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[N:23]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 112183534-Chloro-6-(4-fluorophenyl)pyrimidin-2-amineHCID 11356784HCID 11356784, compound

Product 1

HCID 10180571HCID 10180571, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

2-Phenyl-quinoline-4,6-diamine, 0.5 grams (2.12 mmole) and 4-chloro-6-(4-fluorophenyl)pyrimidin-2-amine, 0.83 grams (4.25 mmole) were weighed directly into a reaction flask and 10 mL of dry N-methyl-2-pyrolidinone and 2 drops of concentrated hydrochloric acid was then added to the flask. The mixture was heated at 100° C. overnight under a nitrogen atmosphere. The mixture was cooled to room temperature and diluted with aqueous sodium hydroxide whereupon a dark brown solid precipitated. The solid was collected and dried under vacuum to yield 0.365 grams of N6-[2-amino-6-(4-fluorophenyl)pyrimidin-4-yl]-2-phenylquinoline-4,6-diamine (92% yield).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customprecipitated
  3. customThe solid was collected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-717b88fdde8b4851b876ec7639bab9c5
Source dataset
uspto-grants-2004_11
Patent number
US06815447B2

Reaction notes

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