Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(4-amino-2-phenylamino-pyrimidin-5-yl)acrylate

HRID 2300058Notes

Reaction equation

HRID 2300058 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[C:17]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18]>O1CCCC1>[NH2:1][C:2]1[C:7]([CH:8]=[CH:22][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 183753114-Amino-2-phenylamino-pyrimidine-5-carboxaldehyde

Product 1

HCID 54291613Ethyl 3-(4-amino-2-phenylamino-pyrimidin-5-yl)acrylateYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 4-amino-2-phenylamino-pyrimidine-5-carboxaldehyde (2.89 g, 13.50 mmol) in 120 mL of tetrahydrofuran was added (carbethoxymethylene)triphenylphosphorane (11.00 g, 31.60 mmol). The reaction mixture was heated at reflux for 9 hours then stirred at room temperature overnight. The solution was concentrated in vacuo and treated with ethyl acetate and hexane to give a yellow solid. The solid was collected by filtration and purified by flash chromatography to give 1.55 g (40%) of ethyl 3-(4-amino-2-phenylamino-pyrimidin-5-yl)acrylate, mp 190-192° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 9 hours
  3. concentrationThe solution was concentrated in vacuo
  4. additiontreated with ethyl acetate and hexane
  5. customto give a yellow solid
  6. filtrationThe solid was collected by filtration
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e027ed9ec2c140068915b233108c9c64
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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