Triethylamine → Tert-butyl 3-(6-chloropyrimidin-4-ylamino)phenylcarbamate

HRID 1053188Notes

Reaction equation

HRID 1053188 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][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.C(N(CC)CC)C>C(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 57708283Tert-butyl 3-(6-chloropyrimidin-4-ylamino)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4,6-Dichloropyrimidine (1.5 g, 10 mmol), tert-butyl 3-aminophenylcarbamate (2.1 g, 10 mmol) and triethylamine (2.2 g, 20 mmol) were mixed in ethanol (20 mL), heated at 80° C. for 16 hr. The reaction mixture was cooled to RT and solvent was removed in vacuo. The gummy crude product was mixed with 20 mL of DCM and was stirred at RT to give an off-white solid, which was filtered and dried under vacuum (1.6 g, 5 mmol). MS (m/z): MH+=321, 323.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customsolvent was removed in vacuo
  3. additionThe gummy crude product was mixed with 20 mL of DCM
  4. customto give an off-white solid, which
  5. filtrationwas filtered
  6. customdried under vacuum (1.6 g, 5 mmol)

Sources & evidence

ORD record
ord-76422ecab2d644c1b0da358a1f40d956
Source dataset
uspto-grants-2016_07
Patent number
US09393246B2

Reaction notes

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