Diisopropylethylamine → tert-butyl 4-fluoro-2-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)phenylcarbamate

HRID 605865Notes

Reaction equation

HRID 605865 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:11]([NH:23][C:24]2[N:29]=[C:28](SC#N)[C:27]([N+:33]([O-:35])=[O:34])=[CH:26][N:25]=2)[CH:10]=1.C(N(CC)C(C)C)(C)C>C1COCC1.CCOC(C)=O>[C:18]([O:17][C:16](=[O:22])[NH:15][C:12]1[CH:13]=[CH:14][C:9]([F:8])=[CH:10][C:11]=1[NH:23][C:24]1[N:25]=[C:26]([NH:1][CH:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)[C:27]([N+:33]([O-:35])=[O:34])=[CH:28][N:29]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 59704889tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate

Product 1

HCID 59705007tert-butyl 4-fluoro-2-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)phenylcarbamateYield 72.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 96 mg (0.95 mmol) of 4-amino-tetrahydropyran in 35 mL anhydrous THF was added 0.35 g (0.86 mmol) tert-butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate, then 0.3 mL N,N-diisopropylethyl amine (1.7 mmol). The slightly cloudy mixture was stirred at room temperature for 3 hrs till HPLC showed the completion of reaction. The mixture became clear then. The reaction mixture was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 0.28 g (˜70% yield) orange-yellow solid as the crude product.

Workup

  1. customthe completion of reaction
  2. washwashed with brine twice
  3. dry with materialdried over Na2SO4
  4. customSolvents were removed under vacuum

Sources & evidence

ORD record
ord-14ce2b311d8d4f90aa2907749485698d
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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