Potassium Carbonate → tert-Butyl [4-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-2-yl]carbamate

HRID 541852Notes

Reaction equation

HRID 541852 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([Cl:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:11]=3)[CH:5]=[CH:6][CH:7]=2)[C:28]([Cl:32])=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961683Tert-butyl {4-[2-(3-aminophenyl)ethyl]pyridin-2-yl}carbamate

Product 1

HCID 57962500tert-Butyl [4-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-2-yl]carbamateYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl {4-[2-(3-aminophenyl)ethyl]pyridin-2-yl}carbamate (160 mg, 0.51 mmol) and 2,4,5-trichloropyrimidine (98.3 mg, 0.54 mol) in N,N-dimethylformamide (2.3 mL) was added potassium carbonate (212 mg, 1.53 mmol). The resultant mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered first to remove K2CO3, followed by quenching 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 water and then dried (Na2SO4), filtered and concentrated to give the residue, which was purified by trituration with cold EtOAc to give the desired product (123 mg, 36%) as an off-white powder. LCMS for C22H24Cl2N5O2 (M+H)+: m/z=460.1, 462.0.

Workup

  1. filtrationThe reaction mixture was filtered first
  2. customto remove K2CO3
  3. customby quenching with water
  4. additionEtOAc was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc twice
  7. washThe combined organic layers were washed with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give the residue, which
  12. customwas purified by trituration with cold EtOAc

Sources & evidence

ORD record
ord-646ce888f4cf49828b2ef361676fc6c9
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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