2-Bromo-4-isopropylaniline → HCID 18323721, compound

HRID 1872031Notes

Reaction equation

HRID 1872031 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[N:14]=1>C(O)CO.C(OCC)(=O)C>[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[N:14]=1

Participants

5

Reactant 2

HCID 5213372-Bromo-4-isopropylanilineHCID 183237602-Chloro-4-methyl-6-(2-thienyl)pyrimidine

Product 1

HCID 18323721HCID 18323721, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Part C: 2-Bromo-4-(1-methylethyl)aniline (0.26 g) and 2-chloro-4-methyl-6-(2-thienyl)pyrimidine (0.21 g) in ethylene glycol were heated at reflux for 24 hours. The reaction mixture was diluted with ethyl acetate, washed with aq. sodium hydroxide solution (10%, 3×100 mL) and the organic phase was dried. Solvent removal gave a crude brown oil, which was purified on silica gel using 20% ethyl acetate in hexanes (Rf 0.5) as eluent to provide N-(2-bromo-4-isopropylphenyl)-4-methyl-6-(2-thienyl)-2-pyrimidinamine (0.1 g) as a solid, mp 98-101° C. Mass spec (NH3 --CI/DDIP); 390 (M+H)+.

Workup

  1. temperatureat reflux for 24 hours
  2. washwashed with aq. sodium hydroxide solution (10%, 3×100 mL)
  3. customthe organic phase was dried
  4. customSolvent removal
  5. customgave a crude brown oil, which
  6. customwas purified on silica gel using 20% ethyl acetate in hexanes (Rf 0.5) as eluent

Sources & evidence

ORD record
ord-b9c99cec20c54dfebfab140c2586002e
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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