Ammonium Chloride → 1-Benzyl-3-(4,5-dimethyl-2-pyrimidyl)indazole

HRID 990815Notes

Reaction equation

HRID 990815 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([Sn](C)(C)C)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:22]1[N:27]=[C:26]([CH3:28])[C:25]([CH3:29])=[CH:24][N:23]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:22]2[N:27]=[C:26]([CH3:28])[C:25]([CH3:29])=[CH:24][N:23]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 125817842-Chloro-4,5-dimethylpyrimidineHCID 158403561-Benzyl-3-trimethylstannylindazole

Product 1

HCID 184166511-Benzyl-3-(4,5-dimethyl-2-pyrimidyl)indazole

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

640 mg of 1-benzyl-3-trimethylstannylindazole (1.72 mmol), 212 mg of 2-chloro-4,5-dimethylpyrimidine* (1.49 mmol) and 72 mg (0.10 mmol) of Pd(PPh3)2Cl2 (5.8 mol %) in 20 ml of toluene were heated under reflux overnight in an argon atmosphere. The mixture was cooled to room temperature, saturated ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and freed from the solvent on a rotary evaporator. Purification was carried out by chromatography over silica gel using cyclohexane/ethyl acetate as the eluent (gradient from 10:1 to 1:1).

Workup

  1. temperatureunder reflux overnight in an argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customfreed from the solvent on a rotary evaporator
  5. customPurification

Sources & evidence

ORD record
ord-f9ca0b8b2f1441e7af2ee373e2979910
Source dataset
uspto-grants-2002_10
Patent number
US06462068B1

Reaction notes

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