4-Chloroaniline → HCID 66679767, compound

HRID 1942966Notes

Reaction equation

HRID 1942966 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Li]CCCC.Cl[C:15]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[C:17]([NH:27][N:28]=[CH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)[N:16]=1>C1COCC1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[C:17]([NH:27][N:28]=[CH:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:32][CH:31]=3)[N:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 86661474HCID 86661474, compound2×HCID 178418339Butyllithium

Product 1

HCID 66679767HCID 66679767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a −78° C. THF solution of 4-chloroaniline was added 1 equivalent of nBuLi to prepare the lithium anilide. The solution was allowed to come to room temperature under nitrogen atmosphere. Aliquots of the lithium anilide were added portion wise to a THF solution of 2-chloro-4-phenyl-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidine (XX) containing 0.05 equivalents (relative to (XX)) of Bis(triphenylphosphine) palladium(II) dichloride. The reaction was followed by thin layer chromatography. When the starting material XX was consumed the reaction was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered and concentrated at reduced pressure. The product, N-(4-chlorophenyl)-4-phenyl-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-2-amine (Example 58) was obtained as a solid. ESI/MS 483.9728, 485.9988 (M+H).

Workup

  1. customTo a −78° C
  2. customto come to room temperature under nitrogen atmosphere
  3. customWhen the starting material XX was consumed the reaction
  4. additionwas poured into a saturated aqueous solution of sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-9092a58caf2a48f4a61598d0c1fb71db
Source dataset
uspto-grants-2013_03
Patent number
US08389718B2

Reaction notes

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