Potassium Carbonate → 1-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione

HRID 858080Notes

Reaction equation

[CH2:1]([N:5]1[C:10]([Cl:11])=[CH:9][C:8](=[O:12])[NH:7][C:6]1=[O:13])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br>CN(C)C=O.[Cl-].[Na+].O>[CH2:1]([N:5]1[C:10]([Cl:11])=[CH:9][C:8](=[O:12])[N:7]([CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[F:20])[C:6]1=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 23 °C

Procedure

The crude product from step 1 (3.0 g, 14.8 mmol) was dissolved in N,N-dimethylformamide (30 mL) and treated with potassium carbonate (4.08 g, 29.6 mmol) and 2-fluorobenzyl bromide (Aldrich) (1.8 ml, 14.8 mmol). The reaction was stirred at 23° C. for 2 hours and then at 48° C. for 3 hours. The reaction was mixed with diluted brine and extracted with ethyl acetate (3×). The combined ethyl acetate extracts were then washed with diluted aqueous sodium chloride solution and brine, dried (sodium sulfate) and concentrated to dryness to afford 1-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione as a yellow oil (4.07 g, 89%). 1H NMR (CDCl3, 200 MHz) δH 0.96 (t, 3H), 1.25–1.48 (m, 2H), 1.58–1.76 (m, 2H), 4.03 (t, 2H), 5.20 (s, 2H), 5.97 (s, 1H), 6.97–7.10 (m, 2H), 7.17–7.30 (m, 2H).

Workup

waitat 48° C. for 3 hours
extractionextracted with ethyl acetate (3×)
washThe combined ethyl acetate extracts were then washed with diluted aqueous sodium chloride solution and brine
dry with materialdried (sodium sulfate)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-7b8ae48fe4464e55895ce9de4efbc515
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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