Dichloromethane → HCID 10734147, compound

HRID 1068569Notes

Reaction equation

[N:1]1([C:10]2[N:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(Cl)Cl>CN(C=O)C.O>[N:1]1([C:10]2[N:11]=[C:12]([Cl:17])[CH:13]=[C:14]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:15]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: -5 °C

Procedure

The obtained 2-(benzimidazol-1-yl)-4,6-dichloropyrimidine (2.08 g, 7.85 mmol) dissolved in DMF(30 ml) was cooled to −5° C., added with anhydrous potassium carbonate (3.0 g, 22 mmol) and morpholine (0.68 g. 7.85 mmol) and stirred for 30 minutes. The reaction mixture was further stirred at room temperature overnight and condensed under reduced pressure. The residue was added with methylene chloride and water and shaken for mixing. The organic layer was separated out and washed with water, dried over anhydrous magnesium sulfate and condensed. The obtained residue was purified by silica gel column chromatography to obtain 1.90 g (yield 77%) of 2-(benzimidazol-1-yl)-4-chloro-6-morpholinopyrimidine with melting point of 178° C.-181° C.

Workup

stirringThe reaction mixture was further stirred at room temperature overnight
customcondensed under reduced pressure
stirringshaken
additionfor mixing
customThe organic layer was separated out and
washwashed with water
dry with materialdried over anhydrous magnesium sulfate and condensed
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ed558616daf14810b89f5f040736a0f6
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251900B1

Reaction notes

Loading…