Sulfuric Acid → 2,4-Di-tert-butyl-6-{4-[3-(4,5-dimethyl-4h-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-pyrimidine mono-sulfate salt

HRID 896228Notes

Reaction equation

HRID 896228 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][S:24][C:25]3[N:29]([CH3:30])[C:28]([CH3:31])=[N:27][N:26]=3)[CH2:17][CH2:16]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[S:32](=[O:36])(=[O:35])([OH:34])[OH:33].C(OCC)(=O)C>C(O)(C)C>[S:32]([OH:36])([OH:35])(=[O:34])=[O:33].[C:1]([C:5]1[N:10]=[C:9]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:8]=[C:7]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][S:24][C:25]3[N:29]([CH3:30])[C:28]([CH3:31])=[N:27][N:26]=3)[CH2:19][CH2:20]2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 114307322-tert-Butyl-4-(4-(3-((4-methyl-5-methyl-4H-(1,2,4)triazol-3-yl)sulfanyl)propyl)piperazin-1-yl)-6-tert-butylpyrimidine

Product 1

HCID 223498562,4-Di-tert-butyl-6-{4-[3-(4,5-dimethyl-4h-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-pyrimidine mono-sulfate saltYield 88.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

2,4-Di-tert-butyl-6-{4-[3-(4,5-dimethyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-pyrimidine (1.0 g, 2.2 mmol) was dissolved in isopropanol at 60° C. A solution of concentrated sulfuric acid (0.22 g, 98%, 2.2 mmol) in isopropanol (1 mL) was added giving a clear solution. Ethyl acetate (20 mL) was slowly added keeping the flask at ˜50° C. The resulting slurry was cooled to ambient temperature and stirred overnight. The precipitate was filtered, rinsed with 10 mL ethyl acetate and vacuum dried at 40° C. overnight to give 2,4-Di-tert-butyl-6-{4-[3-(4,5-dimethyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-pyrimidine mono-sulfate salt (1.06 g). Yield: 86.9%.

Workup

  1. customgiving a clear solution
  2. customat ˜50° C
  3. filtrationThe precipitate was filtered
  4. washrinsed with 10 mL ethyl acetate and vacuum
  5. customdried at 40° C. overnight

Sources & evidence

ORD record
ord-92c59386486c4e6ab0c8949658f3cbd7
Source dataset
uspto-grants-2005_07
Patent number
US06919342B2

Reaction notes

Loading…