Water → HCID 24760508, compound

HRID 1928270Notes

Reaction equation

HRID 1928270 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-1e35a507bee5441ebad82d9f6845cbbe
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

Loading…