2-Bromo-4-isopropylaniline → HCID 10591763, compound

HRID 1872028Notes

Reaction equation

HRID 1872028 reaction equation
BrC1C=C(C)C=CC=1N(C)[C:10]1[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1.[Br:19][C:20]1[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:21]=1[NH2:22]>C(O)CO>[Br:19][C:20]1[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:21]=1[NH:22][C:10]1[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

4

Reactant 2

HCID 5213372-Bromo-4-isopropylanilineHCID 10494830HCID 10494830, compound

Product 1

HCID 10591763HCID 10591763, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Part A: A mixture of the product from Example 1, Part A (2.01 g, 14.01 mmoles), 2-bromo-4-(1-methylethyl)aniline (3 g, 14.10 mmoles) in ethylene glycol (20 mL) was heated to reflux for 1.5 hours. Following cooling to room temperature and partitioning between ethyl acetate (200 mL) and aqueous sodium hydroxide (1 M, 50 mL), the organic layer was washed with brine, dried, and concentrated in vacuo. The residue was chromatographed on silica gel using 5% ethyl acetate in hexanes to give 2-N-(2-bromo-4-(1-methylethyl)phenyl)-4,6-dimethylpyrimidinamine (3.28 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. custompartitioning between ethyl acetate (200 mL) and aqueous sodium hydroxide (1 M, 50 mL)
  4. washthe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel using 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2edd36ee614f439ba4e8d586c637eb17
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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