Water → Tert-butyl {4-chloro-2-fluoro-5-[(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate

HRID 1800763Notes

Reaction equation

HRID 1800763 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([Cl:15])=[CH:10][C:9]=1[F:16])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.Cl[C:28]1[N:33]=[C:32]([S:34][C:35]#[N:36])[C:31]([N+:37]([O-:39])=[O:38])=[CH:30][N:29]=1.O>O1CCCC1>[Cl:15][C:11]1[C:12]([NH:14][C:28]2[N:33]=[C:32]([S:34][C:35]#[N:36])[C:31]([N+:37]([O-:39])=[O:38])=[CH:30][N:29]=2)=[CH:13][C:8]([NH:7][C:6](=[O:17])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[C:9]([F:16])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateHCID 76849224HCID 76849224, compound

Product 1

HCID 86646098Tert-butyl {4-chloro-2-fluoro-5-[(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl(5-amino-4-chloro-2-fluorophenyl)carbamate (5.17 g, 19.8 mmol) in tetrahydrofuran (10 mL) were added N-ethyl-N-isopropylpropane-2-amine (6.93 mL, 39.6 mmol) and 2-chloro-5-nitropyrimidin-4-yl thiocyanate (6.44 g, 29.7 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water (200 mL), and the mixture was extracted with ethyl acetate (300 mL, 50 mL). The combined organic layer was washed with saturated brine (30 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 {4-chloro-2-fluoro-5-[(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate as a yellow amorphous solid. The obtained compound was used for the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (300 mL, 50 mL)
  2. washThe combined organic layer was washed with saturated brine (30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e4c833da052b433cb5c922012cf2dea8
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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