2-Fluorobenzylamine → HCID 58166437, compound

HRID 1405995Notes

Reaction equation

HRID 1405995 reaction equation
[F:1][C:2]1[C:3]([N:13]2[CH:17]=NC=N2)=[N:4][C:5](=[O:12])[N:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:7]=1.[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1CN>O1CCOCC1>[F:1][C:2]1[C:3]([NH:13][CH2:17][C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[F:18])=[N:4][C:5](=[O:12])[N:6]([CH2:8][CH:9]([CH3:10])[CH3:11])[CH:7]=1

Participants

4

Reactant 2

HCID 666492-FluorobenzylamineHCID 58166428HCID 58166428, compound

Product 1

HCID 58166437HCID 58166437, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-fluoro-1-isobutyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (500 mg, 2.1 mmol) and 2-fluorobenzylamine (313 mg, 2.5 mmol) in dry 1,4-dioxane (10 mL) was heated to reflux for 1 h under nitrogen. After cooling to room temperature, the reaction mixture was concentrated in vacuo. Recrystallization from EtOAc/methyl tert-butylether afforded 5-fluoro-4-(2-fluorobenzylamino)-1-isobutylpyrimidin-2(1H)-one (545 mg, 89%) as an off white solid: mp 118-119° C.; 1H NMR (400 MHz, CDCl3) δ 7.45 (td, J=7.6, 1.7 Hz, 1H), 7.35-7.28 (m, 2H), 7.13 (ddd, J=21.9, 13.9, 7.3 Hz, 3H), 5.58 (s, 1H), 4.81 (d, J=5.4 Hz, 2H), 3.56 (d, J=7.5 Hz, 2H), 2.16 (dt, J=13.6, 6.8 Hz, 1H), 0.95 (d, J=6.7 Hz, 6H); ESIMS m/z 295 ([M+H]+).

Workup

  1. temperatureto reflux for 1 h under nitrogen
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customRecrystallization from EtOAc/methyl tert-butylether

Sources & evidence

ORD record
ord-c6096ffad14c466da6aebe52f3672d1b
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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