Triethylamine → HCID 22352269, compound

HRID 896791Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1.[CH:13]1([O:18][C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:22][NH2:23])[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[N:7]=[C:6]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:19]([O:18][CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:20]=2)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

2,4-Dichloro-5-nitro-6-methylpyrimidine (2.0 g) was dissolved in tetrahydrofuran (14 ml), and added with a solution of 3-cyclopentyloxy-4-methoxybenzylamine (2.25 g) dissolved in tetrahydrofuran (7 ml) with stirring and cooling on a salt-ice bath (−10° C.). Then, the mixture was added dropwise with triethylamine (1.4 ml), and stirred for 30 minutes on a salt-ice bath (−10° C.). The reaction mixture was further added with saturated brine, and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the resulting residue was suspended and washed in a mixed solvent of ether and hexane (50:50) to obtain 3.11 g of the title compound.

Workup

stirringstirred for 30 minutes on a salt-ice bath (−10° C.)
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
washwashed in a mixed solvent of ether and hexane (50:50)

Sources & evidence

ORD record: ord-9a7ed4dc81684f309cf87d3c26339c83
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919455B2

Reaction notes

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