Diisopropylethylamine → Tert-butyl (3-((2-chloro-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate

HRID 1482721Notes

Reaction equation

HRID 1482721 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[CH:15][CH:16]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:14]=[CH:15][CH:16]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 59174297Tert-butyl (3-((2-chloro-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichloro-5-fluoropyrimidine (800 mg, 4.8 mmoL), tert-butyl (3-aminophenyl)carbamate (996 mg, 4.8 mmoL) and Hunig's base (948 uL, 5.75 mmoL) were dissolved in THF (20 mL). The reaction mixture was heated at reflux overnight. After cooling, partitioned between water/brine (10 mL), agitated and separated the layers. Dried organic phase over sodium sulfate, and the solvent was removed via rotary evaporation. Titration with EtOAc and Heptane gave after filtration a white solid, 1 g. LC/MS (RT=2.03/(M+1)) 339.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. custompartitioned between water/brine (10 mL)
  5. customseparated the layers
  6. customDried organic phase over sodium sulfate, and the solvent was removed via rotary evaporation
  7. customTitration with EtOAc and Heptane gave
  8. filtrationafter filtration a white solid, 1 g
  9. customLC/MS (RT=2.03/(M+1)) 339.1

Sources & evidence

ORD record
ord-3727a04e1c604226ba000781cee278c6
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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