Citric Acid → HCID 21100056, compound

HRID 917599Notes

Reaction equation

HRID 917599 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[N:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=[O:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCCCCC.O1CCCC1>[Cl:13][C:14]1[N:19]=[C:18]([Cl:20])[C:17]([CH:27]([OH:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)=[CH:16][N:15]=1

Participants

8

Reactant 5

HCID 311Citric AcidHCID 7912DiisopropylamineHCID 142732-PyridinecarboxaldehydeHCID 775312,4-DichloropyrimidineHCID 178418339Butyllithium

Product 1

HCID 21100056HCID 21100056, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a 1.6 M solution of n-butyl lithium in hexane 19.3 ml is dropped over a period of 10 minutes a solution of diisopropylamine 3.1 g in tetrahydrofuran 80 ml in a dry ice-acetone bath and the mixture is stirred for 30 minutes. To the mixture is dropped over a period of 2.5 hours a solution of 2,4-dichloropyrimidine 2 g in tetrahydrofuran 70 ml and the mixture is stirred at the same temperature for 1 hour. To the mixture is dropped pyridine-2-aldehyde 2.2 g in tetrahydrofuran 20 ml over a period of 50 minutes, and the mixture is stirred at the same temperature for 1 hour. The reaction mixture is poured into a 10% aqueous citric acid solution and the organic layer is separated, washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue is purified with silica gel chromatography (solvent; chloroform:methanol=10:1, hexane:ethyl acetate=3:2, hexane:ethyl acetate=2:1) to give crude 2,4-dichloro-5-[(hydroxy)(2-pyridyl)methyl]pyrimidine 480 mg.

Workup

  1. stirringthe mixture is stirred at the same temperature for 1 hour
  2. stirringthe mixture is stirred at the same temperature for 1 hour
  3. customthe organic layer is separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified with silica gel chromatography (solvent; chloroform:methanol=10:1, hexane:ethyl acetate=3:2, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e1b9cfce07f24b5eb890f6aeb39e0c71
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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