Ethyl 2-formylbutanoate → HCID 178457579, compound

HRID 1253164

Reaction equation

HRID 1253164 reaction equation
Cl.[CH2:2]([N:5]=[C:6]([NH2:21])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH2:20])=[NH:19])[N:9]=1)[CH2:3][CH3:4].[Na].[CH:23]([CH:25]([CH2:31][CH3:32])[C:26](OCC)=O)=[O:24]>CO>[CH2:2]([N:5]=[C:6]([NH2:21])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[N:20]=[C:23]([OH:24])[C:25]([CH2:31][CH3:32])=[CH:26][N:19]=2)[N:9]=1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 289299Ethyl 2-formylbutanoateHCID 5360545SodiumHCID 201371495-(4-[2-Propylguanidino]pyrimid-2-yl)valeramidine hydrochloride

Product 1

HCID 178457579HCID 178457579, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-(4-[2-propylguanidino]pyrimid-2-yl)valeramidine hydrochloride (0.4 g.) and the sodium salt of ethyl 2-formylbutyrate (1.5 g.) in MeOH (5 ml.) was heated under reflux for 4 hours. The solvent was evaporated in vacuo and the residue was partitioned between water (pH 7) and EtOAc. The EtOAc layer was separated, dried (MgSO4) and evaporated in vacuo to give 2-[4-(4-(2-propylguanidino]pyrimid-2-yl)butyl]-5-ethyl-4-hydroxypyrimidine as an oil (0.13 g.) which was characterised by conversion to the bis hydrogen maleate salt (0.11 g.), m.p. 140°-142°.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between water (pH 7) and EtOAc
  4. customThe EtOAc layer was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d6b062b552241ad9e238f1746723804
Source dataset
uspto-grants-1988_05
Patent number
US04748165

Linked notes

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