Ethyl Acetate → HCID 57677586, compound

HRID 492685Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[OH:19].C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[C:6]([O:19][C:11]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=2[Cl:9])[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

4-Amino-6-chloropyrimidine (648 mg) was dissolved in N,N-dimethylformamide (5 ml), and 2-chloro-4-nitrophenol (1.736 g) and N,N-diisopropylethylamine (3.48 ml) were added thereto, followed by stirring at 160° C. overnight. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and a 1 N aqueous solution of sodium hydroxide. The organic layer was washed with a 1 N aqueous solution of sodium hydroxide and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reducer pressure to give a residue, to which ethyl acetate (10 ml) was then added to precipitate crystals. The crystals were filtered and dried under aeration to provide the titled compound (230 mg, 17%) as pale yellow crystals.

Workup

temperatureThe reaction mixture was cooled down to room temperature
custompartitioned between ethyl acetate
washThe organic layer was washed with a 1 N aqueous solution of sodium hydroxide and brine in this order
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under a reducer pressure
customto give a residue
customto precipitate crystals
filtrationThe crystals were filtered
customdried under aeration

Sources & evidence

ORD record: ord-99fe201064414a71b577c0cb9e440a8b
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531532B2

Reaction notes

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