Triethyl orthoacetate → 3-(4-((2-(adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-2,6-dimethyl-pyrimidin-4(3H)-one

HRID 56214Notes

Reaction equation

HRID 56214 reaction equation
[C:1]12([CH2:11][CH2:12][NH:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:26])/[CH:22]=[C:23](\[NH2:25])/[CH3:24])=[CH:16][C:15]=3[F:27])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:28](OCC)(OCC)(OCC)[CH3:29]>>[C:1]12([CH2:11][CH2:12][NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[C:21](=[O:26])[CH:22]=[C:23]([CH3:24])[N:25]=[C:28]4[CH3:29])=[CH:16][C:15]=3[F:27])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 117966106(Z)-N-(4-((2-(adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-3-aminobut-2-enamide

Product 1

HCID 900229623-(4-((2-(adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-2,6-dimethyl-pyrimidin-4(3H)-oneYield 3%

Conditions

Temperature
150 °C

Procedure

A mixture of (Z)—N-(4-((2-(adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-3-aminobut-2-enamide (0.31 g, 0.83 mmol) and triethyl orthoacetate (20 mL) was stirred at 150° C. for 12 h. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a red brown solid (10 mg, 3%). The compound was characterized by the following spectroscopic data:

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Sources & evidence

ORD record
ord-3151ad68060645269d3198a65c3b0456
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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