Carbon Dioxide → 2,4,6-Trichloropyrimidine-5-carboxylic acid

HRID 917622Notes

Reaction equation

HRID 917622 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[N:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[N:15]=1.[C:22](=[O:24])=[O:23].Cl>CCCCCC.O1CCCC1.[Cl-].[Na+]>[C:22]([C:17]1[C:16]([Cl:21])=[N:15][C:14]([Cl:13])=[N:19][C:18]=1[Cl:20])([OH:24])=[O:23]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 773782,4,6-TrichloropyrimidineHCID 178418339Butyllithium

Product 1

HCID 200839572,4,6-Trichloropyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A mixture of diisopropylamine 2.54 g, a 1.6M solution of n-butyl lithium in hexane 15.7 ml and tetrahydrofuran 100 ml is stirred for 30 minutes on a dry ice-acetone bath. Thereto is added 2,4,6-trichloropyrimidine 2.00 g in tetrahydrofuran 8 ml over a period of 30 minutes, followed by further one hour agitation. The reaction mixture is poured into dry ice, and the mixture is stirred for a hour at room temperature. The reaction mixture is made acidic with 10% hydrochloric acid 20 ml, diluted with an aqueous saturated sodium chloride solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The solvent is removed by azeotrope with chloroform and the resulting hemisolid is triturated with hexane to give 5-carboxy-2,4,6-trichloropyrimidine as a crystalline powder, 1.51 g. mp 150-153° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe solvent is removed by azeotrope with chloroform
  6. customthe resulting hemisolid is triturated with hexane

Sources & evidence

ORD record
ord-7085751fddfa434fa6dc2f92cb5bddde
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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