Triethylamine → HCID 178446283, compound

HRID 616251Notes

Reaction equation

HRID 616251 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([OH:12])[N:3]=1.Cl.[NH2:14][C:15]([CH2:23][CH3:24])([CH2:21][CH3:22])[C:16](=[N:19][OH:20])[CH2:17][OH:18].C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([OH:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:14][C:15]([CH2:23][CH3:24])([CH2:21][CH3:22])[C:16](=[N:19][OH:20])[CH2:17][OH:18])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737620833-Amino-3-ethyl-1-hydroxy-pentan-2-one oxime hydrochlorideHCID 178418667HCID 178418667, compound

Product 1

HCID 178446283HCID 178446283, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-amino-4-chloro-6-hydroxy-5-nitropyrimidine (III) (Hal=Cl) (2.3 g) in dry ethanol was treated with 3-amino-1-hydroxy-3-spirocyclohexylpropan-2-one oxime hydrochloride (IV) (2.5g) and dry triethylamine (2.7 g) and the mixture was refluxed for 7 h. The reaction mixture was filtered and the solid washed with hot ethanol. The solvent was removed from the filtrate and the resulting yellow oil was triturated with cold water giving a yellow solid which on recrystallisation from water in the presence of charcoal gave the nitropyrimidine (II) (1.85 g; yield 47.4%) as an off-white powder, m.pt >300° (decomp.).

Workup

  1. temperaturethe mixture was refluxed for 7 h
  2. filtrationThe reaction mixture was filtered
  3. washthe solid washed with hot ethanol
  4. customThe solvent was removed from the filtrate
  5. customthe resulting yellow oil was triturated with cold water giving a yellow solid which
  6. customon recrystallisation from water in the presence of charcoal

Sources & evidence

ORD record
ord-13acd8104d604aac909e38f8259b518f
Source dataset
uspto-grants-1978_02
Patent number
US04073786

Reaction notes

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