Hydrochloric Acid → HCID 22640009, compound

HRID 2415100Notes

Reaction equation

HRID 2415100 reaction equation
Cl.C([O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][NH:15][C:16]2[C:21]([Cl:22])=[C:20]([CH3:23])[N:19]=[C:18]([CH3:24])[N:17]=2)=[CH:12][CH:11]=1)C1C=CC=CC=1.Cl.[OH-].[Na+]>C(O)C>[Cl:22][C:21]1[C:16]([NH:15][CH2:14][C:13]2[CH:25]=[CH:26][C:10]([OH:9])=[CH:11][CH:12]=2)=[N:17][C:18]([CH3:24])=[N:19][C:20]=1[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22640014HCID 22640014, compound

Product 1

HCID 22640009HCID 22640009, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

112 g (0.286 mol) of (4-benzyloxybenzyl)(5-Chloro-2,6-dimethylpyrimidin-4-yl)amine hydrochloride (from example A1) are suspended in ethanol (1.1 l) and 12.5 N hydrochloric acid (1.1 l) and the suspension is heated at reflux for 1 h. The yellow solution is cooled to room temperature and stirred into ice-water (4 l). The solution is then adjusted to a pH of 8 using 10 N sodium hydroxide solution and extracted with ethyl acetate (3×1 l). The combined organic extracts are washed with water (1 l), dried over sodium sulfate and concentrated to a volume of about 100 ml. The residue is taken up in ethyl acetate (100 ml) and diisopropyl ether (200 ml) and stirred at room temperature for 15 min. The crystals are filtered and washed with diisopropyl ether/ethyl acetate) (2:1). Drying in a vacuum drying cabinet at 40° C. gives 38.4 g (51%) of the title compound as a pale beige solid. m.p.: 202° C.

Workup

  1. temperatureat reflux for 1 h
  2. extractionextracted with ethyl acetate (3×1 l)
  3. washThe combined organic extracts are washed with water (1 l)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a volume of about 100 ml
  6. filtrationThe crystals are filtered
  7. washwashed with diisopropyl ether/ethyl acetate) (2:1)
  8. customDrying in a vacuum
  9. customdrying cabinet at 40° C.

Sources & evidence

ORD record
ord-de96eadd09564f28b4c15a996c2a638f
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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