Ethyl Acetate → [4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amine

HRID 1242489Notes

Reaction equation

C(O[C:4](=O)[N:5]([CH2:7][C:8]1[C:9]([CH:24]2[CH2:26][CH2:25]2)=[N:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[N:12][CH:13]=1)C)C.[OH-].[K+].O.NN.CCOC(C)=O>C(O)CO>[CH:24]1([C:9]2[C:8]([CH2:7][NH:5][CH3:4])=[CH:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=3)[N:10]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 210 °C

Procedure

0.83 g (2.2 mmol) of [4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-carbamic acid ethyl ester was dissolved in 15 ml of ethylene glycol. Then, 1.72 g (26.4 mmol) of potassium hydroxide (86%) and 0.44 ml=0.46 g (9.0 mmol) of hydrazine hydrate were added and the reaction mixture heated up to 190° C. (oil bath, 210° C.) for 90 minutes. After cooling down below 80° C., some pieces of ice were added to the reaction mixture followed by EtOAc. It was then extracted twice with EtOAc; the combined organic phases were washed with water, dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of MeCl2, MeOH) to give 0.59 g of the title compound as yellow solid.

Workup

temperatureAfter cooling down below 80° C.
additionsome pieces of ice were added to the reaction mixture
extractionIt was then extracted twice with EtOAc
washthe combined organic phases were washed with water
dry with materialdried over anhydrous magnesium sulfate
customevaporated
customThe crude product was purified by flash chromatography (SiO2, gradient of MeCl2, MeOH)

Sources & evidence

ORD record: ord-abe0b800514b4f2c8998d650cca58040
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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