Dimethylformamide → HCID 21833515, compound

HRID 1740864Notes

Reaction equation

[CH3:1][C:2]1[C:3]([O:15][CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:7]=1[CH3:8].CN(C)C=O.[H-].[Na+].[CH:33]1([CH2:36]Br)[CH2:35][CH2:34]1>C(Cl)(Cl)Cl>[CH:33]1([CH2:36][N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:18])[CH2:16][O:15][C:3]2[C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=[C:5]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:4]=2)[CH2:35][CH2:34]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2-(5,6-dimethyl-2-phenyl-4-pyrimidinyloxy)-N-phenylacetamide (1.5 g) obtained in Example 189 and dimethylformamide (30 ml) is added sodium hydride (about 60% oily, 0.2 g) at 0-5° C., and the mixture is stirred at 0° C. for one hour. To the mixture is added cyclopropylmethyl bromide (0.67 g) at the same temperature, and the mixture is stirred at room temperature for two hours. To the reaction solution are added chloroform and ice-water, and the chloroform layer is collected, washed with water, and dried over anhydrous sodium sulfate. The chloroform layer is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from isopropanol to give the desired compound (1.56 g), m.p. 119-121° C.

Workup

stirringthe mixture is stirred at room temperature for two hours
customthe chloroform layer is collected
washwashed with water
dry with materialdried over anhydrous sodium sulfate
concentrationThe chloroform layer is concentrated under reduced pressure
customthe residue is purified by silica gel column chromatography (eluent; chloroform)
customrecrystallized from isopropanol

Sources & evidence

ORD record: ord-ed23cab0814443a4a6f36193fdbce53e
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972946

Reaction notes

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