Aniline → HCID 1484283, compound

HRID 2367171Notes

Reaction equation

HRID 2367171 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>C(O)C>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 655222-Amino-4,6-dichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 1484283HCID 1484283, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To 4,6-dichloro-2-pyrimidinamine (0.50 g, 3.05 mmol) in ethanol (EtOH) (10 mL) was added aniline (0.3 mL, 3.3 mmol) and the reaction mixture was stirred overnight at 100° C. The mixture was poured onto ethyl acetate (EtOAc) and saturated aqueous NaHCO3. The layers were separated and the aqueous layer was further extracted with more EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to provide the crude title compound (620 mg) as a yellow solid. Product contains ˜25% of bis-addition product. LC-MS (ES) m/z=221 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with more EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7e1927c5fda2425599bf43b99e09c931
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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