Hydrochloric Acid → HCID 22732347, compound

HRID 1765124Notes

Reaction equation

HRID 1765124 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1.Cl.[OH-].[Na+]>O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:2]2[CH:3]=[C:4]([CH3:14])[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[N:7]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 27633954-Chloro-6-methyl-2-(pyridin-2-yl)pyrimidine

Product 1

HCID 22732347HCID 22732347, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6-chloro-4-methyl-2-(2-pyridinyl)pyrimidine (15 mg, 0.56 mmol), p-anisidine (68 mg, 0.55 mmol) in water (10 mL) was added 2 N HCl (0.3 mL). The mixture was refluxed for 6 h, cooled to room temperature, and neutralized with 2N NaOH to pH 10. The resulting mixture was then extracted with 1:1 Hexane/EtOAc (50 mL). The organic phase was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (1:1 Hexane/EtOAc) to yield the product as a tan solid (72 mg, 45%). 1H NMR (CDCl3): 8.80 (d, J=4.5 Hz, 1H), 8.45 (d, J=8.1 Hz, 1H), 7.81 (m, 1H), 7.35 (m, 1H), 7.23 (d, J=8.4 Hz, 2H), 7.12 (s, 1H), 6.93 (d, J=8.4 Hz, 2H), 6.41 (s, 1H), 3.83 (s, 3H), 2.45 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. extractionThe resulting mixture was then extracted with 1:1 Hexane/EtOAc (50 mL)
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (1:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-e1662cb0a6964953aeb2b8d18dc5c01c
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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