2,4,6-Trichloropyrimidine → 2,6-Dichloro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 415440Notes

Reaction equation

HRID 415440 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.Cl.[CH3:11][O:12][C:13]1[NH:17][N:16]=[C:15]([NH2:18])[CH:14]=1>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:18][C:15]2[CH:14]=[C:13]([O:12][CH3:11])[NH:17][N:16]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 2

HCID 773782,4,6-TrichloropyrimidineHCID 178493289HCID 178493289, compound

Product 1

HCID 1784930502,6-Dichloro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amineYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4,6-trichloro-pyrimidine (1.7 g) in absolute ethanol (100 mL) was added DIEPA (4.1 mL) and 5-methoxy-1H-pyrazol-3-amine hydrogen chloride salt (1.46 g). The resulting solution was stirred at room temperature for over night. The solvent was evaporated under reduced pressure. The crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes) to give the titled compound as solid (1.23 g). 1H NMR δ 12.19 (s, 1H) 10.68 (s, 1H) 6.76 (s, 1H) 5.40 (s, 1H) 3.82 (s, 3H); m/z 260.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes)

Sources & evidence

ORD record
ord-dbc94f7fa6114182a36cb1499267bc72
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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