Water → HCID 24760508, compound

HRID 1989548Notes

Reaction equation

HRID 1989548 reaction equation
CC1[N:3]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]4[CH:25]=[C:24]([C:26]5[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=5)[CH:23]=[C:22]([CH3:36])[N:21]=4)[N:15]=3)=[CH:10][CH:9]=2)C(C)=CC=1.Cl.NO.[OH-].[Na+].O>C(O)CC>[CH3:36][C:22]1[N:21]=[C:20]([C:16]2[N:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([NH2:3])=[N:13][CH:12]=3)[CH:19]=[CH:18][N:17]=2)[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:28][CH:27]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 57469006HCID 57469006, compound

Product 1

HCID 24760508HCID 24760508, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Step 3) The title compound was prepared from the above described 4-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-3-yl]-2-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidine (0.250 g, 1.29 mmol) by heating with hydroxylamine hydrochloride (259 mg, 3.86 mmol) in a mixture of aqueous NaOH (1.5 M, 0.86 mL, 1.29 mmol) in 1-propanol (2.5 mL) in a sealed tube at 120° C. for 4 h. Cooled to rt, added some water and extracted twice with AcOEt, dried over Na2SO4, filtered off and evaporated totally. The crude material was triturated with ether to give the title compound (0.140 g, 67%) as an off-white solid. MS (ISP) 408.3 [(M+H)+]; mp 258° C.

Workup

  1. customStep 3) The title compound was prepared from the
  2. extractionextracted twice with AcOEt
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered off
  5. customevaporated totally
  6. customThe crude material was triturated with ether

Sources & evidence

ORD record
ord-dc45b30022074986a0fae92e6269203b
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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