Dimethyl Sulfide → HCID 86600785, compound

HRID 1391840Notes

Reaction equation

HRID 1391840 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1.[CH3:15][S:16][CH3:17].[Cl:18]N1C(=O)CCC1=O>ClCCl.C(#N)C>[ClH:18].[CH3:14][O:13][C:5]1[N:4]2[N:3]=[C:2]([N:1]=[S:16]([CH3:17])[CH3:15])[N:10]=[C:9]2[C:8]([O:11][CH3:12])=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 114468885,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

Product 1

HCID 86600785HCID 86600785, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

2-Amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (5.6 g, 0.029 mol) was slurried in dichloromethane (100 mL) and methyl sulfide (1.9 g, 0.031 mol) was added. The mixture was cooled to −25° C., and a solution of N-chlorosuccinimide (4.2 g, 0.031 mol) in acetonitrile (40 mL) was added to the reaction slurry over one hour, keeping the internal temperature at −22 to −28° C. When the addition was complete, the reaction was allowed to warm to room temperature over several hours. The new slurry was filtered and the solids washed with acetonitrile (2×40 mL). The solids were dried in a vacuum oven to provide 7.7 g of N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-S,S-dimethylsulfilimine hydrochloride as a light tan solid, m.p. 170-174° C. The material was 95 area % pure by HPLC, with the remainder being the amine starting material.

Workup

  1. customat −22 to −28° C
  2. additionWhen the addition
  3. temperatureto warm to room temperature over several hours
  4. filtrationThe new slurry was filtered
  5. washthe solids washed with acetonitrile (2×40 mL)
  6. customThe solids were dried in a vacuum oven

Sources & evidence

ORD record
ord-b1534eba62d84dedbaa9fbd1d77dc86d
Source dataset
uspto-grants-2008_03
Patent number
US07339058B2

Reaction notes

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