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2,4,6-Trichloropyrimidine → 2,6-Dichloropyrimidin-4-yl-(5-isopropyl-1H-pyrazol-3-yl)-amine

HRID 1510399
Notes
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Reaction equation

HRID 1510399 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH:10]([C:13]1[NH:17][N:16]=[C:15]([NH2:18])[CH:14]=1)([CH3:12])[CH3:11].C(N(C(C)C)CC)(C)C>C(O)CCC>[Cl:1][C:2]1[N:3]=[C:4]([NH:18][C:15]2[CH:14]=[C:13]([CH:10]([CH3:12])[CH3:11])[NH:17][N:16]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 773782,4,6-TrichloropyrimidineHCID 81531DiisopropylethylamineHCID 27695273-(propan-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 578664512,6-Dichloropyrimidin-4-yl-(5-isopropyl-1H-pyrazol-3-yl)-amineYield 86.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,4,6-trichloropyrimidine (1.8 g, 9.8 mmol), 5-isopropyl-1H-pyrazol-3-ylamine (1.25 g, 10.0 mmol), diisopropylethylamine (3 mL, 18 mmol) and 1-butanol (10 mL) was heated to 80° C. for 2 h, at which point LC/MS indicated that the reaction was complete. The solvents were removed on a rotary evaporator and the paste was treated with ethyl acetate. The organic solution was washed with water and brine and dried over magnesium sulfate. The residue was concentrated on a rotary evaporator, and the pale yellow solid that remained was purified via flash chromatography to yield the desired product (2.3 g, 70%) as an off white solid.

Workup

  1. customThe solvents were removed on a rotary evaporator
  2. additionthe paste was treated with ethyl acetate
  3. washThe organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe residue was concentrated on a rotary evaporator
  6. customthe pale yellow solid that remained was purified via flash chromatography

Sources & evidence

ORD record
ord-75d5dfc59da147f28eb5bbc5c29ddcd5
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08211929B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes