Methanol → Ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoate

HRID 2406956Notes

Reaction equation

HRID 2406956 reaction equation
CO.[C:3]([C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1)(=O)[CH2:4][CH2:5][CH3:6].[F:19][C:20]([F:35])([F:34])[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:32]=[CH:31][C:30]([NH2:33])=[CH:29][N:28]=2)=[CH:23][CH:22]=1.[B][B][B][B][B][B][B][B][B][B]>Cl>[F:35][C:20]([F:19])([F:34])[C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]=[CH:29][C:30]([NH:33][CH:3]([C:8]3[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=3)[CH2:4][CH2:5][CH3:6])=[CH:31][N:32]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 431422772-(4-(Trifluoromethyl)phenyl)pyrimidin-5-amineHCID 67980577Ethyl 4-butyrylbenzoateHCID 178419135HCID 178419135, compound

Product 1

HCID 67981358Ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoateYield 24%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methanol (0.70 mL) was added to a flask containing ethyl 4-butyrylbenzoate (82.8 mg, 0.376 mmol), 2-(4-(trifluoromethyl)phenyl)pyrimidin-5-amine (90.0 mg, 0.376 mmol) and decaborane (46.0 mg, 0.376 mmol) at room temperature under nitrogen. The resulting solution was stirred at room temperature overnight. The mixture was diluted with 1N HCl and extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-35% ethyl acetate in heptane) gave ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoate (40.0 mg, 24%). 1H NMR (400 MHz, CDCl3, δ): 8.32 (d, J=8.19 Hz, 2 H), 8.07 (s, 2 H), 7.98-8.04 (m, 2 H), 7.63 (d, J=8.19 Hz, 2 H), 7.36-7.41 (m, 2 H), 4.38-4.43 (m, 2 H), 4.35 (q, J=7.02 Hz, 2 H), 1.75-1.91 (m, 2 H), 1.36 (t, J=7.02 Hz, 3 H), 1.20-1.52 (m, 2 H), 0.94 (t, J=7.32 Hz, 2 H). MS (M+1): 444.3.

Workup

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (0-35% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a44cfc1e3bcd463c8bbcad3577117ca4
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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