Hydrochloric Acid → HCID 22732493, compound

HRID 1765208Notes

Reaction equation

HRID 1765208 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=1[NH2:18].Cl.[OH-].[Na+]>O.C(O)C>[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=1[NH:18][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68962,6-DimethylanilineHCID 14798Sodium HydroxideHCID 27633954-Chloro-6-methyl-2-(pyridin-2-yl)pyrimidine

Product 1

HCID 22732493HCID 22732493, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-6-methyl-2-(2-pyridinyl)pyrimidine (50 mg, 0.243 mmol), 2,6-dimethylaniline (45 μl, 0.365 mmol) and 2N HCl (150 μl) in water:ethanol (2:1, 10 ml) was refluxed for 24 h. The mixture was cooled to room temperature and basified with aqueous 2N NaOH to pH 10–12. The mixture was extracted with ethyl acetate (75 ml), which was washed with water (2×20 ml), aqueous saturated NaCl (1×20 ml), and dried over anhydrous sodium sulfate. The ethyl acetate solution was rotary evaporated to dryness and the residue was purified by column chromatography to give a yellow oil (58 mg, 82%). 1H NMR (CDCl3): 8.81–8.78 (m, 1H), 8.47 (d, J=8.1 Hz, 1H), 7.83–7.77 (m, 1H), 7.36–7.30 (m, 1H), 7.21–7.13 (m, 3H), 6.91 (s, 1H), 5.77 (s, 1H), 2.39 (s, 3H), 2.23 (s, 6H).

Workup

  1. temperaturewas refluxed for 24 h
  2. extractionThe mixture was extracted with ethyl acetate (75 ml), which
  3. washwas washed with water (2×20 ml), aqueous saturated NaCl (1×20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe ethyl acetate solution was rotary evaporated to dryness
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-420cb91f62164b73b97a077af008770f
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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