Sodium → HCID 178430498, compound

HRID 2291333Notes

Reaction equation

HRID 2291333 reaction equation
Cl.[F:2][C:3]([F:22])([F:21])[CH2:4][N:5]=[C:6]([NH2:20])[NH:7][C:8]1[N:12]=[CH:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH2:19])=[NH:18])[N:9]=1.[Na].[CH:24]([CH:26]([CH3:32])[C:27](OCC)=O)=[O:25]>CO>[OH:25][C:24]1[C:26]([CH3:32])=[CH:27][N:19]=[C:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:10]2[CH:11]=[N:12][C:8]([NH:7][C:6]([NH2:20])=[N:5][CH2:4][C:3]([F:2])([F:21])[F:22])=[N:9]2)[N:18]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10898741Ethyl 2-FormylpropionateHCID 21279721HCID 21279721, compound

Product 1

HCID 178430498HCID 178430498, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-(3-[2-(2,2,2-trifluoroethyl)guanidino]-1,2,4-triazol-1-yl)valeramidine hydrochloride (1 g.) in MeOH (14 ml.) was treated with the sodium salt of ethyl 2-formylpropionate (1.95 g.) and the suspension heated under reflux for 3.5 hours. This suspension was evaporated and the residue partitioned between water and ether. The aqueous layer was acidified with glacial HOAc to pH 3 and further extracted with ether. Neutralisation with aqueous ammonia (s.g. 0.880) and extraction with EtOAc gave a white solid which was crystallised twice from acetonitrile to give 4-hydroxy-5-methyl-2-[4-(3-[2-(2,2,2-trifluoroethyl)guanidino]-1,2,4-triazol-1-yl)butyl]pyrimidine (0.127 g.; 12%), m.p. 235°-237°.

Workup

  1. temperaturethe suspension heated
  2. temperatureunder reflux for 3.5 hours
  3. customThis suspension was evaporated
  4. customthe residue partitioned between water and ether
  5. extractionfurther extracted with ether
  6. extractionNeutralisation with aqueous ammonia (s.g. 0.880) and extraction with EtOAc
  7. customgave a white solid which
  8. customwas crystallised twice from acetonitrile

Sources & evidence

ORD record
ord-4da51636c65d4d37b4e1a7b88965735d
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

Loading…