Ethyl Acetate → 5-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-(1,1-bis(ethoxycarbonyl)prop-3-yl)pyrimidine

HRID 1766081Notes

Reaction equation

HRID 1766081 reaction equation
[C:1]([C:3]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[N:5][C:6]([S:11][CH3:12])=[N:7][C:8]=1[CH:9]=[CH2:10])#[N:2].[C:21](=[O:24])([O-:23])[O-].[K+].[K+].[CH2:27](C(CC)(C([O-])=O)C([O-])=O)[CH3:28].[CH3:38][CH2:39][O:40][C:41]([CH3:43])=[O:42]>C(O)C.C1(C)C=CC=CC=1.Cl>[C:1]([C:3]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[N:5][C:6]([S:11][CH3:12])=[N:7][C:8]=1[CH2:9][CH2:10][CH:43]([C:41]([O:40][CH2:39][CH3:38])=[O:42])[C:21]([O:23][CH2:27][CH3:28])=[O:24])#[N:2]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69515632,2-DiethylpropanedioateHCID 211090865-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-vinyl-pyrimidine

Product 1

HCID 211090855-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-(1,1-bis(ethoxycarbonyl)prop-3-yl)pyrimidine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

5-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-vinyl-pyrimidine (example 25a) was dissolved in a mixture of ethanol (2 ml) and toluene (2 ml). Potassium carbonate (690 mg) and diethylmalonate (272 μl) were added and the mixture was stirred at room temperature for 4 h. The reaction mixture was then poured in a mixture of 0.5M aq. HCl (25 ml) and EtOAc (50 ml). The organic layer was washed with H2O (50 ml) and sat. aq. NaCl (50 ml), dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with toluene/EtOAC=100/0 to 95/5 (v/v) as eluent.

Workup

  1. washThe organic layer was washed with H2O (50 ml) and sat. aq. NaCl (50 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe title compound was purified by chromatography on silica gel with toluene/EtOAC=100/0 to 95/5 (v/v) as eluent

Sources & evidence

ORD record
ord-22c5850948a84a268cdf232a3a50e7e0
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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