Potassium Carbonate → HCID 57962703, compound

HRID 541898Notes

Reaction equation

HRID 541898 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:6]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH:7]=1.[Cl:32][C:33]1[N:38]=[C:37](Cl)[C:36]([F:40])=[CH:35][N:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:28]([O:27][C:25]([NH:24][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:35]2[C:36]([F:40])=[CH:37][N:38]=[C:33]([Cl:32])[N:34]=2)=[CH:7][C:6]=1[CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 57962696Carbamic acid,n-[3-[2-[5-amino-2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]ethyl]phenyl]-,1,1-dimethylethyl ester

Product 1

HCID 57962703HCID 57962703, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl [3-(2-{5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)phenyl]carbamate (0.4 g, 0.9 mmol) and 2,4-dichloro-5-fluoropyrimidine (0.156 g, 0.936 mmol) in N,N-dimethylformamide (7 mL) was added potassium carbonate (0.662 g, 4.79 mmol). The resultant mixture was stirred overnight at rt overnight. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography to give the desired product (0.32 g, 61%). LCMS for C28H33ClFNaN5O4 (M+Na)+: m/z=580.2.

Workup

  1. customThe reaction was quenched with water
  2. additionEtOAc was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-56d109a745d2482cacc80cea500a6b26
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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