Hydrochloric Acid → HCID 22732493, compound

HRID 2084154Notes

Reaction equation

HRID 2084154 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-b1c4489fe4a74325b6e26af68b231e7f
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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