2,4-Dichloropyrimidine → HCID 178434332, compound

HRID 855624Notes

Reaction equation

HRID 855624 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[NH:4][N:3]=1.C([O-])(O)=O.[Na+].[Cl:17][C:18]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1>C1COCC1.C(O)C>[Cl:17][C:18]1[N:23]=[C:22]([NH:11][C:7]2[CH:6]=[C:5]3[C:10]([C:2]([CH3:1])=[N:3][NH:4]3)=[CH:9][CH:8]=2)[CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 178434350HCID 178434350, compound

Product 1

HCID 178434332HCID 178434332, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-methyl-6-aminoindazole (2.71 g, 0.015 mol) and NaHCO3 (1.26 g, 0.045 mol) in THF (15 mL) and ethanol (60 mL) was added 2,4-dichloropyrimidine (6.66 g, 0.045 mol) at room temperature. After the reaction was stirred for four hours, the suspension was filtered and washed thoroughly with ethanol. The filtrate was concentrated under reduced pressure, and the resulting solid was washed with ether to remove excess pyrimidine to yield 3.5 g (89% yield) of N-(2-chloro-4-pyrimidinyl)-N-(3-methyl-1H-indazol-6-yl)amine.

Workup

  1. filtrationthe suspension was filtered
  2. washwashed thoroughly with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthe resulting solid was washed with ether
  5. customto remove excess pyrimidine

Sources & evidence

ORD record
ord-29bd22c63143425d9ff5236b3bcbe392
Source dataset
uspto-grants-2007_08
Patent number
US07262203B2

Reaction notes

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