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

HRID 1510399Notes

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

Participants

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

customThe solvents were removed on a rotary evaporator
additionthe paste was treated with ethyl acetate
washThe organic solution was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationThe residue was concentrated on a rotary evaporator
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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