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

HRID 1078201Notes

Reaction equation

HRID 1078201 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(OC)=O)=[C:12]([N:19]([CH3:21])[CH3:20])[N:11]=[CH:10][N:9]=1)(=O)[CH3:2].Cl.[NH2:26][OH:27].[C:28]([O-:31])(=[O:30])C.[Na+].[CH3:33]O>>[CH3:33][O:31][C:28](=[O:30])[CH:8]([O:7][C:6]1[CH:22]=[CH:23][CH:24]=[C:4]([C:1](=[N:26][OH:27])[CH3:2])[CH:5]=1)[C:13]1[CH:14]=[N:9][CH:10]=[N:11][C:12]=1[N:19]([CH3:20])[CH3:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54226209Methyl 4-(3-acetylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate

Product 1

HCID 86749729Methyl-[3-(1-hydroximinoethyl)-phenoxy]-6-dimethylamino-pyrimidin-5-yl-acetate

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 -[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-e149ccc3ce0a455c81d4c9509d0ca615
Source dataset
uspto-grants-1996_08
Patent number
US05547919

Reaction notes

Loading…