Water → HCID 21891803, compound

HRID 858081Notes

Reaction equation

Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH2:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:14]([N:18]1[C:23](Cl)=[CH:22][C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:19]1=[O:34])[CH2:15][CH2:16][CH3:17].C(N(CC)CC)C.O>CN1CCCC1=O>[CH2:14]([N:18]1[C:23]([NH:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=2)=[CH:22][C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:19]1=[O:34])[CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-(4-nitro-phenyl)-ethylamine hydrochloride salt (Fluka) (7.85 g, 38.7 mmol), 1-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione (8.0 g, 25.8 mmol) and triethylamine (10.7 mL, 77 mmol) in N-methyl-pyrrolidin-2-one (200 mL) was stirred at 75° C. for 16 hours. The reaction was then mixed with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were dried (magnesium sulfate) and concentrated. Column chromatography afforded 1-butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione (4.7 g, 41%) as a solid. 1H NMR (CDCl3, 200 MHz) δH 0.84 (t, 3H), 1.11–1.50 (m, 4H), 3.10 (t, 2H), 3.48 (m, 2H), 3.70 (t, 2H), 4.36 (t, 1H), 4.94 (t, 1H), 5.20 (s, 2H), 6.95–7.10 (m, 2H), 7.17–7.30 (m, 2H), 7.39 (d, 2H), 8.20 (d, 2H).

Workup

extractionextracted with ethyl acetate (3×)
dry with materialThe combined ethyl acetate layers were dried (magnesium sulfate)
concentrationconcentrated

Sources & evidence

ORD record: ord-079bf66084924f779f454b534324519e
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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