Hydrochloric Acid → AF-353 hydrochloride

HRID 18674Notes

Reaction equation

HRID 18674 reaction equation
[I:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.[ClH:22]>C(O)(C)C>[ClH:22].[I:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 159538025-(5-Iodo-2-isopropyl-4-methoxyphenoxy)pyrimidine-2,4-diamine2×

Product 1

HCID 46837686AF-353 hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine A mixture of 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (240 g, 0.60 mol) in 1.2 L of isopropanol was heated to 70° C. An aqueous solution of 6N HCl was added dropwise to the reaction mixture, and the slurry was heated to 75° C. for two hours. The slurry was cooled to 20° C. and aged. Precipitated solids were collected by filtration, washed with cold isopropanol, and dried in a vacuum oven (50° C., 24 inches Hg) to give 232 g of -(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine hydrochloride salt, 98% yield: m.p. 262.0-263.0 degrees C.; 1HNMR (DMSO) δ=1.2 (d, 6H), 3.1 (m, 1H), 3.85 (s, 3H), 6.95 (s, 1H), 7.25 (s, 1H), 7.45 (s, 1H), 7.6 (s, 2H), 8.25 (s, 1H), 8.6 (s, 1H), 11.9 (s, 1H).

Workup

  1. temperaturethe slurry was heated to 75° C. for two hours
  2. temperatureThe slurry was cooled to 20° C.
  3. customPrecipitated solids
  4. filtrationwere collected by filtration
  5. washwashed with cold isopropanol
  6. customdried in a vacuum oven (50° C., 24 inches Hg)

Sources & evidence

ORD record
ord-21f8165974e6441dba34aaca96d71575
Source dataset
uspto-grants-2010_06
Patent number
US07741484B2

Reaction notes

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