2,4-Dichloropyrimidine → 2-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 2102815Notes

Reaction equation

HRID 2102815 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=1.C(N(C(C)C)C(C)C)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 231324822-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amineYield 19.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 2,4-dichloropyrimidine (0.967 g, 6.49 mmol), 3-amino-5-methylpyrazole (0.63 g, 6.40 mmol), and ethyldiisopropylamine (2.8 mL, 16.22 mmol) in ethanol (13 mL) was stirred at −10° C. for 2 h, then at r.t. overnight, and finally at 50° C. for 3.5 h. The mixture was concentrated to a total volume of approximately 10 mL. Upon repeated addition of diethylether, (2-chloropyrimidin-4-yl)-(5-methylpyrazol-3-yl)amine (0.258 g, 1.23 mmol, 19%) was obtained as colourless crystals. LC/ESI-MS: m/z=210 [M(35Cl)+H]+; m/z=208 [M(35Cl)−H]−; Rt=230 min.

Workup

  1. waitat r.t. overnight, and finally at 50° C. for 3.5 h
  2. concentrationThe mixture was concentrated to a total volume of approximately 10 mL
  3. additionaddition of diethylether

Sources & evidence

ORD record
ord-22ed6f52820d4127b7ca3a9095359328
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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