Ethanol → HCID 86614568, compound

HRID 1766089Notes

Reaction equation

HRID 1766089 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([CH:9]([C:17]([O-:19])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8].[C:20]([C:22]1[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)=[N:24][C:25]([S:30][CH3:31])=[N:26][C:27]=1C=C)#[N:21].[CH3:41][CH2:42]O>C1(C)C=CC=CC=1.C(Cl)Cl.CCOC(C)=O>[C:20]([C:22]1[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)=[N:24][C:25]([S:30][CH3:31])=[N:26][C:27]=1[CH2:8][CH2:7][CH:9]([C:17]([O:19][CH2:41][CH3:42])=[O:18])[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])#[N:21]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 21109084HCID 21109084, compoundHCID 85608643HCID 85608643, compound

Product 1

HCID 86614568HCID 86614568, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21877217Toluene methylene chlorideSolvent

Procedure

Potassium carbonate (1.88 g) and tert-butyl ethylmalonate were suspended in EtOH (82 ml) and a solution of 5-cyano-2-methylthio-4-(3-nitro-phenyl)-6-vinylpyrimidine (example 27b, 2.71 g) in toluene/CH2Cl2 (33 ml) was slowly added (ca 1.5 h). After the addition was complete, the mixture was stirred for an additional 40 min. The mixture was diluted with EtOAc and washed with water (2×) and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/CH2Cl2=1/1 (v/v) as eluent.

Workup

  1. additionAfter the addition
  2. washwashed with water (2×) and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe title compound was purified by chromatography on silica gel with hept/CH2Cl2=1/1 (v/v) as eluent

Sources & evidence

ORD record
ord-9bf84ca3af0c4590b086e1e7c126b7e8
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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