Diisopropylethylamine → HCID 86646092, compound
Reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.Cl[C:27]1[N:32]=[C:31]([S:33][C:34]#[N:35])[C:30]([N+:36]([O-:38])=[O:37])=[CH:29][N:28]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[N+:36]([C:30]1[C:31]([S:33][C:34]#[N:35])=[N:32][C:27]([NH:15][C:10]2[CH:9]=[C:8]([NH:7][C:6](=[O:16])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:13]=[CH:12][C:11]=2[CH3:14])=[N:28][CH:29]=1)([O-:38])=[O:37]Participants
Procedure
To a solution of tert-butyl(3-amino-4-methylphenyl)carbamate (8.82 g, 39.7 mmol) in tetrahydrofuran (200 mL) were added N-ethyl-N-isopropylpropane-2-amine (10.4 mL, 59.8 mmol) and 2-chloro-5-nitropyrimidin-4-yl thiocyanate (9.49 g, 43.8 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (200 mL), and the mixture was extracted with ethyl acetate (150 mL, 2×30 mL). The combined organic layer was washed with saturated brine (20 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give tert-butyl {3-[(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]-4-methylphenyl}carbamate as a yellow amorphous solid. The obtained compound was used for the next reaction without further purification.
Workup
- extractionthe mixture was extracted with ethyl acetate (150 mL, 2×30 mL)
- washThe combined organic layer was washed with saturated brine (20 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe insoluble material was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c0d49202e710486da71a04e1ed08fc4e
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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