4-Fluorobenzylamine → HCID 54681990, compound

HRID 720297Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][OH:23])[CH2:17][CH2:16]2)[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=O)C.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>CN(C=O)C>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:4]([C:6]2[N:7]=[C:8]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][OH:23])[CH2:17][CH2:16]3)[N:9]([CH3:14])[C:10](=[O:13])[C:11]=2[OH:12])=[O:3])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 70 °C

Procedure

5-Hydroxy-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.024 g, 0.074 mmol) was dissolved in DMF (1 mL) to which was added 4-fluoro-benzyl amine (0.047 mL, 0.37 mmol). The mixture was stirred at 70° C. for 2 hours. The resulting mixture was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as a white powder (0.0149 g, 50% yield). 1H NMR (500 MHz, MeOD) δ: 8.81 (1H, bs), 7.40 (2H, dd, J=8.5, 5.5 Hz), 7.08 (2H, t, J=8.8 Hz), 4.59 (2H, d, J=6.1 Hz), 3.94 (2H, t, J=5.2 Hz), 3.70 (4H, d, J=11.3 Hz), 3.58 (3H, s), 3.47–3.35 (6H, m). HRMS (M+H) calcd for C19H25FN4O5: 406.18907. found: 406.1895.

Workup

customThe resulting mixture was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record: ord-04f3b81020994784bf6eeade26036b9c
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135467B2

Reaction notes

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