Triethyl orthoacetate → 2-(dihexylamino)-5-(2,4-dimethyl-6-oxopyrimidin-1(6H)-yl)benzonitrile

HRID 56209Notes

Reaction equation

[NH2:1]/[C:2](/[CH3:28])=[CH:3]\[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:9]([C:26]#[N:27])[CH:8]=1)=[O:5].[C:29](OCC)(OCC)(OCC)[CH3:30]>>[CH2:14]([N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:4](=[O:5])[CH:3]=[C:2]([CH3:28])[N:1]=[C:29]2[CH3:30])=[CH:8][C:9]=1[C:26]#[N:27])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Reactant 2

HCID 66221Triethyl orthoacetate

HCID 90022969(Z)-3-amino-N-(3-cyano-4-(dihexylamino)phenyl)but-2-enamide

Product 1

HCID 729501742-(dihexylamino)-5-(2,4-dimethyl-6-oxopyrimidin-1(6H)-yl)benzonitrileYield 4%

Conditions

Temperature: 150 °C

Procedure

A mixture of (Z)-3-amino-N-(3-cyano-4-(dihexylamino)phenyl)but-2-enamide (1.30 g, 3.38 mmol) and triethyl orthoacetate (30 mL) was stirred at 150° C. overnight. The mixture was then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=50:1) to give the title compound as pale yellow oil (60 mg, 4%). The compound was characterized by the following spectroscopic data:

Workup

temperatureThe mixture was then cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=50:1)

Sources & evidence

ORD record: ord-d8ff107012df4ccd936fc716ad28fe87
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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