Sodium Carbonate → HCID 59586799, compound

HRID 1897650Notes

Reaction equation

HRID 1897650 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[CH:5]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]([Cl:18])=[CH:13][N:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO.CCOC(C)=O>[Cl:10][C:11]1[N:16]=[C:15]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)[C:14]([Cl:18])=[CH:13][N:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 59586799HCID 59586799, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-cyclopropyl-1H-pyrazol-3-amine (246 mg, 2.00 mmol), 2,4,5-trichloropyrimidine (367 mg, 2.00 mmol, 1 equiv.) and Na2CO3 (233 mg, 2.20 mmol, 1.1 equiv.) in EtOH (10 mL) was heated at 40° C. for 16 h. The crude reaction mixture was diluted with EtOAc and sequentially washed with: water (3×) and saturated aqueous NaCl (1×). The resulting EtOAc layer was dried over Na2SO4 and then concentrated in vacuo, providing 2,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine; ESMS m/z 270.0 (M+H+).

Workup

  1. customThe crude reaction mixture
  2. washsequentially washed with: water (3×) and saturated aqueous NaCl (1×)
  3. dry with materialThe resulting EtOAc layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5824c28ab24a443ba48b2089a48f0e43
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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