Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-ethyl-3-(4-(ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylate

HRID 1666254Notes

Reaction equation

HRID 1666254 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[C:8]([CH3:12])[N:7]=[C:6]([S:13][CH3:14])[N:5]=1)[CH3:2].[C:15]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:17][CH2:18][CH3:19])=[O:16]>C1COCC1>[CH2:18]([O:17][C:15](=[O:16])/[CH:20]=[CH:10]/[C:9]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]([S:13][CH3:14])=[N:7][C:8]=1[CH3:12])[CH3:19]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 576069534-(Ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 57606958(E)-ethyl-3-(4-(ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde (38 g, 180 mmol) in THF (500 mL) was added (Carbethoxymethylene) triphenylphosphorane (95%, Aldrich, 85.18 g, 244 mmol). The reaction mixture was heated to reflux for 1.5 h and was monitored by TLC (4:1 hexanes/ethylacetate). The reaction was cooled to room temperature and was concentrated on a rotary evaporator. It was directly subjected to column chromatography (4:1 hexanes/ethylacetate) to give (E)-ethyl-3-(4-(ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylate as a white crystal, 46.14 g (91% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 h
  3. concentrationwas concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-e0443520573d4d27a62daeb816ef39ef
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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