HCID 53866493, compound → HCID 54559865, compound

HRID 647115Notes

Reaction equation

HRID 647115 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:10]1[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=1)[C:6]([O:8]C)=[O:7])[CH3:2].C(ON=C(C1N=C(N)C=CN=1)C(OCC)=O)C>[OH-].[Na+]>[CH2:1]([O:3][N:4]=[C:5]([C:10]1[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 53866493HCID 53866493, compoundHCID 54347666HCID 54347666, compound

Product 1

HCID 54559865HCID 54559865, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture (930 mg) of methyl 2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetate (syn isomer) and ethyl 2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetate (syn isomer) in 1 N aqueous sodium hydroxide (4.95 ml) was stirred for 3.5 hours at ambient temperature. The solution was passed through an ion exchange resin [16 ml, Amberlite IRC-50 (trademark: Prepared by Rohm and Haas Co.)] and evaporated to dryness. The residue was triturated in a mixed solvent of acetone (20 ml) and water (2 ml) to give 2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetic acid (syn isomer) (0.8 g), mp. 180° to 182° C. (dec.).

Workup

  1. customThe solution was passed through an ion exchange resin [16 ml, Amberlite IRC-50 (trademark: Prepared by Rohm and Haas Co.)]
  2. customevaporated to dryness
  3. customThe residue was triturated in a mixed solvent of acetone (20 ml) and water (2 ml)

Sources & evidence

ORD record
ord-b7c12c004efc46078ffe1b751cb429d2
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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