Hydrochloric Acid → 4-[(5-Chloro-2,6-dimethylpyrimidin-4-ylamino)methyl]-2-methoxyphenol

HRID 2415102Notes

Reaction equation

HRID 2415102 reaction equation
C([O:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][NH:14][C:15]2[C:20]([Cl:21])=[C:19]([CH3:22])[N:18]=[C:17]([CH3:23])[N:16]=2)=[CH:11][C:10]=1[O:26][CH3:27])C1C=CC=CC=1.Cl>C(O)C>[Cl:21][C:20]1[C:15]([NH:14][CH2:13][C:12]2[CH:24]=[CH:25][C:9]([OH:8])=[C:10]([O:26][CH3:27])[CH:11]=2)=[N:16][C:17]([CH3:23])=[N:18][C:19]=1[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22640039(4-Benzyloxy-3-methoxybenzyl)(5-chloro-2,6-dimethylpyrimidin-4-yl)amine

Product 1

HCID 226400084-[(5-Chloro-2,6-dimethylpyrimidin-4-ylamino)methyl]-2-methoxyphenolYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In analogy to the method described in example B1, 3.0 g (7.8 mmol) of (4-benzyloxy-3-methoxy-benzyl)(5-chloro-2,6-dimethylpyrimidin-4-yl)amine (from example A3) are reacted with 30 ml of 12.5N hydrochloric acid in 30 ml of ethanol. Extraction with ethyl acetate at a pH of 8 gives, after concentration, a solid residue which is chromatographed on silica gel (mobile phase: toluene/dioxane=5:1). Crystallization with toluene gives 1.38 g (60%) of the title compound as a beige crystallizate. m.p.: 179-181.5° C.

Workup

  1. extractionExtraction with ethyl acetate at a pH of 8
  2. customgives
  3. concentrationafter concentration
  4. customa solid residue which is chromatographed on silica gel (mobile phase: toluene/dioxane=5:1)
  5. customCrystallization with toluene

Sources & evidence

ORD record
ord-e84ab9daeb2c425b894178571f27cc9c
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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