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

HRID 929823Notes

Reaction equation

HRID 929823 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-12c42ff9997048fcbf14b8889e22d5f5
Source dataset
uspto-grants-2016_03
Patent number
US09296704B2

Reaction notes

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