Triethyl orthoacetate → 3-(3-trifluoromethyl-4-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56236Notes

Reaction equation

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

Participants

Reactant 2

HCID 66221Triethyl orthoacetate

HCID 90024162(Z)-3-amino-N-(3-trifluoromethyl-4-morpholinophenyl)but-2-enamide

Product 1

HCID 900238863-(3-trifluoromethyl-4-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-oneYield 70%

Conditions

Temperature: 150 °C

Procedure

A mixture of (Z)-3-amino-N-(3-trifluoromethyl-4-morpholinophenyl)but-2-enamide (4.0 g, 12.1 mmol) and triethyl orthoacetate (10 mL) was stirred at 150° C. overnight. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (3.00 g, 70%). The compound was characterized by the following spectroscopic data:

Workup

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

Sources & evidence

ORD record: ord-ba1c5d5cbe08443c89b0f722fa30537f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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