2,4-Dichloropyrimidine → HCID 178434332, compound

HRID 1640703Notes

Reaction equation

HRID 1640703 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-1aa047ee8e32422c92e36fd97f0ee409
Source dataset
uspto-grants-2012_02
Patent number
US08114885B2

Reaction notes

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