Water → Tert-butyl {3-[cyclopropyl(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate

HRID 1800715Notes

Reaction equation

HRID 1800715 reaction equation
[CH:1]1([NH:4][C:5]2[CH:6]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.Cl[C:29]1[N:34]=[C:33]([S:35][C:36]#[N:37])[C:32]([N+:38]([O-:40])=[O:39])=[CH:31][N:30]=1.O>O1CCCC1>[CH:1]1([N:4]([C:29]2[N:34]=[C:33]([S:35][C:36]#[N:37])[C:32]([N+:38]([O-:40])=[O:39])=[CH:31][N:30]=2)[C:5]2[CH:6]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH:8]=[CH:9][CH:10]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateHCID 86646082Tert-butyl [3-(cyclopropylamino)phenyl]carbamate

Product 1

HCID 86646084Tert-butyl {3-[cyclopropyl(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [3-(cyclopropylamino)phenyl]carbamate (5.51 g, 15.4 mmol) in tetrahydrofuran (100 mL) were added N-ethyl-N-isopropylpropane-2-amine (8.06 mL, 46.2 mmol) and 2-chloro-5-nitropyrimidin-4-yl thiocyanate (6.66 g, 30.7 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water (100 mL), and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with saturated brine (30 mL), and filtered through a silica gel pad. The obtained filtrate was concentrated under reduced pressure to give tert-butyl {3-[cyclopropyl(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate as a brown amorphous solid. The obtained compound was used for the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  2. washThe combined organic layer was washed with saturated brine (30 mL)
  3. filtrationfiltered through a silica gel pad
  4. concentrationThe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6161a7e505b14b2e8cc4705d90285613
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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