Acetonitrile → 7-(Benzylthio)-5-chloropyrazolo[1,5-a]pyrimidine

HRID 624729Notes

Reaction equation

HRID 624729 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[CH2:12]([SH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(#N)C>O>[CH2:12]([S:19][C:6]1[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=[C:2]([Cl:1])[CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidine

Product 1

HCID 583137227-(Benzylthio)-5-chloropyrazolo[1,5-a]pyrimidineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the reaction flask, 5,7-dichloropyrazolo[1,5-a]pyrimidine (4.1 g, 22 mmol) was added along with benzyl mercaptan (2.8 mL, 22 mmol), triethylamine (3.1 mL, 22 mmol), and acetonitrile (71 mL). The reaction was stirred at room temperature for 3 hours then diluted with water, filtered and washed with water. The product, 7-(benzylthio)-5-chloropyrazolo[1,5-a]pyrimidine, was collected as a solid in 96% yield after drying under vacuum overnight. LCMS (M+1=276)

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customThe product, 7-(benzylthio)-5-chloropyrazolo[1,5-a]pyrimidine, was collected as a solid in 96% yield
  4. customafter drying under vacuum overnight

Sources & evidence

ORD record
ord-e454c213931c4285bb85b567161dc124
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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