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

HRID 1800695Notes

Reaction equation

HRID 1800695 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]#[N:10])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][CH3:27])=[CH:22][C:21]=1[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].O>O1CCCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:27])[C:2]2[N:7]=[C:6]([S:8][C:9]#[N:10])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=2)=[CH:22][C:21]=1[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateHCID 86646076Tert-butyl [2-fluoro-5-(methylamino)phenyl]carbamate

Product 1

HCID 86646077Tert-butyl {2-fluoro-5-[methyl(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2-chloro-5-nitropyrimidin-4-yl thiocyanate (2.73 g, 12.6 mmol) and sodium hydrogen carbonate (2.76 g, 32.9 mmol) in tetrahydrofuran (80 mL) was added a solution of tert-butyl [2-fluoro-5-(methylamino)phenyl]carbamate (2.63 g, 11.0 mmol) produced above in tetrahydrofuran (20 mL), and the mixture was stirred for 1.5 hr. To the reaction mixture was added water (100 mL), and the mixture was extracted with ethyl acetate (100 mL, 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 {2-fluoro-5-[methyl(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 (100 mL, 30 mL)
  2. washThe combined organic layer was washed with saturated brine (20 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-afd011a4d94d40d7ab7b164a858c4090
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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