Triethylamine → HCID 22352269, compound

HRID 1582024Notes

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 tetrahydro-furan (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-eccf97a8086d4783b2106ef4913063c8
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734187B1

Reaction notes

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