Pyridine → HCID 86748893, compound

HRID 1756786Notes

Reaction equation

HRID 1756786 reaction equation
N[C:2]1[C:3]([O:12][CH:13]([CH3:15])[CH3:14])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[N:16]1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(Cl)Cl>[CH3:11][CH:9]([O:8][C:7]1[C:2]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:3]([O:12][CH:13]([CH3:14])[CH3:15])[N:4]=[C:5]([NH2:16])[N:6]=1)[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 15585367HCID 15585367, compound

Product 1

HCID 86748893HCID 86748893, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.42 g of 5-amino-4, 6-di (1-methylethoxy) pyrimidine, 0.30 g of pyridine and 8 ml of methylene chloride was dropwise added 0.26 g of ethyl chloroformate at room temperature with stirring, and the resultant mixture was stirred for 5 hours. The reaction mixture was washed with water and saturated saline in order, dried over anhydrous sodium sulfate and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate-n-hexane (1:5) to give 0.29 g of 4, 6-di (1-methylethoxy)-5-ethoxycarbonyl-aminopyrimidine.

Workup

  1. customat room temperature
  2. washThe reaction mixture was washed with water and saturated saline in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent evaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with ethyl acetate-n-hexane (1:5)

Sources & evidence

ORD record
ord-0500e4935c5f4734beb9c66b196a028a
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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