Dimethylamine → Methyl 4-(3-acetylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate

HRID 1078200Notes

Reaction equation

Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:14][C:15]([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([OH:23])[CH:22]=1)=[O:16].C([O-])([O-])=O.[K+].[K+].[CH3:30][N:31](C=O)[CH3:32].CNC>>[C:15]([C:17]1[CH:22]=[C:21]([CH:20]=[CH:19][CH:18]=1)[O:23][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([N:31]([CH3:32])[CH3:30])[N:5]=[CH:4][N:3]=1)(=[O:16])[CH3:14]

Participants

Reactant 5

HCID 674Dimethylamine

HCID 6228Dimethylformamide

HCID 84873-Hydroxyacetophenone

HCID 11430Potassium Carbonate

HCID 54165419Methyl 2-(4,6-dichloropyrimidin-5-yl)acetate

Product 1

HCID 54226209Methyl 4-(3-acetylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 4,6-dichloropyrimidin-5-yl-acetate (221 g, 1 mol), 3-hydroxyacetophenone (136 g, 1 mol) and K2CO3 (207 g, 1.5 mol) in DMF (150 mol) is stirred at 100° C. for 90 minutes. The dark mixture is cooled to 0° C. and dimethylamine (450 ml of a 40% aqeous solution) is added. Stirring is continued at room temperature for hours. Dilution with water and extraction with ether gives methyl 4-(3-acetylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate as a brownish oil (purity>95%).

Workup

temperatureThe dark mixture is cooled to 0° C.
stirringStirring
waitis continued at room temperature for hours
extractionDilution with water and extraction with ether

Sources & evidence

ORD record: ord-0c182dc3a772413f8fa280e2d836c213
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05547919

Reaction notes

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