Ethyl Acetate → HCID 178434689, compound

HRID 2291327Notes

Reaction equation

HRID 2291327 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]=[C:7]([S:9][CH2:10][CH2:11][CH2:12][OH:13])[NH:6][N:5]=1.CS([C:17]1[N:22]=[C:21]([NH:23][C:24]([NH2:31])=[N:25][CH2:26][C:27]([F:30])([F:29])[F:28])[CH:20]=[CH:19][N:18]=1)=[O:16].CC[O:34][C:35]([CH3:37])=[O:36]>C(O)(C)(C)C>[OH2:13].[C:12]([OH:13])(=[O:16])/[CH:11]=[CH:10]\[C:35]([OH:34])=[O:36].[CH3:3][C:4]1[N:8]=[C:7]([S:9][CH2:10][CH2:11][CH2:12][O:13][C:17]2[N:22]=[C:21]([NH:23][C:24]([NH2:31])=[N:25][CH2:26][C:27]([F:28])([F:29])[F:30])[CH:20]=[CH:19][N:18]=2)[NH:6][N:5]=1.[CH3:3][C:4]1[N:8]=[C:7]([S:9][CH2:10][CH2:11][CH2:12][O:13][C:17]2[N:22]=[C:21]([NH:23][C:24]([NH2:31])=[N:25][CH2:26][C:27]([F:28])([F:29])[F:30])[CH:20]=[CH:19][N:18]=2)[NH:6][N:5]=1.[C:35]([OH:34])(=[O:36])/[CH:37]=[CH:11]\[C:12]([OH:13])=[O:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 212797752-Methylsulphinyl-4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimidineHCID 178434690HCID 178434690, compound

Product 1

HCID 178434689HCID 178434689, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of sodium hydride (50% w/w dispersion in mineral oil; 0.04 g.) in t-butanol (5 ml.) was added 3-methyl-5-(3-hydroxypropylthio)-1,2,4-triazole (0.17 g.) and 2-methylsulphinyl-4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimidine (0.14 g.) (European patent publication No. 30092). The mixture was heated under reflux for 3 hours and evaporated to dryness. The residue was partitioned between EtOAc and 2N aqueous hydrochloric acid. The acid extract was basified with 2N aqueous sodium hydroxide and extracted with EtOAc. This extract was dried (MgSO4) and evaporated to dryness. The residual gum was purified by preparative thin layer chromatography using EtOAc/MeOH/aqueous ammonia (s.g. 0.880) 6:1:1 v/v/v as eluant. Material isolated from the appropriate band was dissolved in EtOAc, filtered and the filtrate treated with a solution of maleic acid (0.1 g.) in EtOAc to give 3-methyl-5-(3-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yloxy]propylthio)-1,2,4-triazole hydrogen maleate hemihydrate (0.05 g.), m.p. 157°-161° (decomp.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customevaporated to dryness
  4. customThe residue was partitioned between EtOAc and 2N aqueous hydrochloric acid
  5. extractionThe acid extract
  6. extractionextracted with EtOAc
  7. dry with materialThis extract was dried (MgSO4)
  8. customevaporated to dryness
  9. customThe residual gum was purified by preparative thin layer chromatography
  10. customMaterial isolated from the appropriate band
  11. filtrationfiltered
  12. additionthe filtrate treated with a solution of maleic acid (0.1 g.) in EtOAc

Sources & evidence

ORD record
ord-3de31966c09d42c9a5e0e225dda1e078
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

Loading…