Hydroxyamine hydrochloride → Methyl 4-[3-(1-hydroximinoethyl)-phenoxy]-6-dimethylamino-pyrimidin-5-yl-acetate

HRID 1957176Notes

Reaction equation

HRID 1957176 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][C:8]1[C:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]([N:19]([CH3:21])[CH3:20])[N:11]=[CH:10][N:9]=1)(=O)[CH3:2].Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>CO>[N:26](=[C:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][C:8]1[C:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]([N:19]([CH3:21])[CH3:20])[N:11]=[CH:10][N:9]=1)[CH3:2])[OH:27]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54226209Methyl 4-(3-acetylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate

Product 1

HCID 86752928Methyl 4-[3-(1-hydroximinoethyl)-phenoxy]-6-dimethylamino-pyrimidin-5-yl-acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The methyl 4-(3-acetylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate obtained is dissolved in 500 ml methanol, and hydroxylamine hydrochloride (76 g, 1.1 mol) and sodium acetate (107 g, 1.3 mol) are added at 0° C. After stirring for 2 hours at room temperature the product is crystallized by adding water. Filtering and drying gives methyl 4-[3-(1-hydroximinoethyl)-phenoxy]-6-dimethylamino-pyrimidin-5-yl-acetate in form of yellowish crystals (292 g) having a m.p. of 113°-115° C.

Workup

  1. customis crystallized
  2. additionby adding water
  3. filtrationFiltering
  4. customdrying

Sources & evidence

ORD record
ord-4ee86eb3d03b4491a8eed6008de93aa6
Source dataset
uspto-grants-1998_07
Patent number
US05783580

Reaction notes

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