Hydrochloric Acid → HCID 57833579, compound

HRID 729982Notes

Reaction equation

HRID 729982 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[N:22]=[C:21](Cl)[CH:20]=[C:19]([Cl:24])[N:18]=1.Cl>O.CC(O)C>[Cl:24][C:19]1[N:18]=[C:17]([NH2:16])[N:22]=[C:21]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)=[CH:10][CH:11]=2)[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 655222-Amino-4,6-dichloropyrimidineHCID 230230754-(2-Methyl-4-pyridinyloxy)aniline

Product 1

HCID 57833579HCID 57833579, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

{4-[(2-Methylpyridin-4-yl) oxy] phenyl} amine (47.5 g, 237 mmol) and 2-amino-4,6-dichloropyrimidine (40.8 g, 249 mmol) were suspended in water (900 mL) and 2-propanol (300 mL). 2M aqueous hydrochloric acid solution (23.7 mL) was then added and the mixture was then heated at 95° C. for 17 h. The mixture was then allowed to come to rt and solids were collected by suction filtration and washed with small amount of isopropanol. The solids were then resuspended in DMF and heated at 90° C. Triethylamine (20 mL) was then added and the mixture was stir for additional 10 min at 90° C. Water was then added in excess until cloudiness persisted at temperature. This was cooled to about 5° C. and precipitate formed were collected by suction filtration, washed with water and dried in vacuum oven at 40° C. to afford desired product (50 g, 64%) as light tan solid. 1H NMR (DMSO-d6) δ 9.40 (s, 1H), 8.27 (d, 1H), 7.76 (d, 2H), 7.06 (d, 2H), 6.75 (brs, 2H), 6.72 (d, 1H), 6.66 (s, 1H), 5.98 (s, 1H); MS ES 328 (M+H)+, calcd 328, RT=1.45 min.

Workup

  1. customto come to rt
  2. filtrationsolids were collected by suction filtration
  3. washwashed with small amount of isopropanol
  4. temperatureheated at 90° C
  5. additionTriethylamine (20 mL) was then added
  6. additionWater was then added in excess until cloudiness
  7. temperatureThis was cooled to about 5° C.
  8. customprecipitate formed
  9. filtrationwere collected by suction filtration
  10. washwashed with water
  11. customdried in vacuum oven at 40° C.

Sources & evidence

ORD record
ord-bc9a37c2300241ee80bb4fe1e05c7731
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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