Methylamine → Diethyl 4-(4-methylaminoquinazolin-2-yl)benzylphosphonate

HRID 54899Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([C:12]1[CH:26]=[CH:25][C:15]([CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:14][CH:13]=1)=O)#[N:2].[CH3:27][NH2:28]>C1COCC1>[CH3:27][NH:28][C:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:9]=[C:10]([C:12]2[CH:26]=[CH:25][C:15]([CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)[N:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A 3.7 g portion of diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzylphosphonate and 10 ml of a 40% aqueous methylamine solution were dissolved in 50 ml of THF and refluxed with heating at 70° C. for 30 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: chloroform: methanol=100:1) and the crude crystals obtained were recrystallized from chloroform-n-hexane to provide 1.0 g of the objective compound as colorless crystals. Table 1 also shows the structure and physical property (melting point) of the compound thus obtained.

Workup

temperaturerefluxed
customAfter completion of the reaction
distillationthe solvent was distilled off under reduced pressure
customthe crude crystals obtained
customwere recrystallized from chloroform-n-hexane

Sources & evidence

ORD record: ord-04ab774150684ddb8ee7e1056c7b006a
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624918

Reaction notes

Loading…