2-Methoxyethanol → N-phenylpyrimidin-2-amine

HRID 1871352Notes

Reaction equation

HRID 1871352 reaction equation
Cl.Br[C:3]1[CH:8]=[C:7](C(C)C)[CH:6]=[CH:5][C:4]=1[NH:12][C:13]([NH2:15])=[NH:14].[C:16](=O)([O-])[O-].[Na+].[Na+].CO[CH2:24][CH2:25]O>C(OCC)(=O)C>[NH:12]([C:13]1[N:14]=[CH:25][CH:24]=[CH:16][N:15]=1)[C:4]1[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 10340Sodium CarbonateHCID 178439245HCID 178439245, compound

Product 1

HCID 11643997N-phenylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Part B: A mixture of the product from part A (1.09 g), 2-bromo-4-isopropylphenylguanidine hydrochloride (1.17 g), and sodium carbonate (424 mg) in 2-methoxyethanol (30 mL) was refluxed for 19 hr. The cooled reaction mixture was diluted with ethyl acetate and washed with water (2×) and brine, dried and evaporated. The crude reaction product was chromatographed on silica gel using 50% petroleum ether in methylene chloride as eluent. The intermediate anilinopyrimidine was obtained as an oil (337 mg). CI Mass Spec. (M+H)+ =462.

Workup

  1. temperaturewas refluxed for 19 hr
  2. customThe cooled reaction mixture
  3. washwashed with water (2×) and brine
  4. customdried
  5. customevaporated
  6. customThe crude reaction product
  7. customwas chromatographed on silica gel using 50% petroleum ether in methylene chloride as eluent

Sources & evidence

ORD record
ord-fa38b7cf068d4f8b863f9d03e8ce3950
Source dataset
uspto-grants-2000_08
Patent number
US06103737

Reaction notes

Loading…