Dimethylformamide → 7-Benzyloxy-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 1830575Notes

Reaction equation

HRID 1830575 reaction equation
[H-].[Na+].[OH:3][C:4]1[N:9]2[N:10]=[CH:11][CH:12]=[C:8]2[N:7]=[C:6]([S:13][CH3:14])[C:5]=1[C:15]#[N:16].CN(C=O)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([O:3][C:4]1[N:9]2[N:10]=[CH:11][CH:12]=[C:8]2[N:7]=[C:6]([S:13][CH3:14])[C:5]=1[C:15]#[N:16])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178503357HCID 178503357, compound

Product 1

HCID 220480797-Benzyloxy-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrileYield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

80 mg of sodium hydride (60%) was added to 400 mg of 7-hydroxy-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile and 6 ml of DMF, followed by stirring at room temperature for about 10 minutes, and then 350 mg of benzyl bromide was added thereto, followed by stirring at about 50° C. overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, about 50 ml of water was added thereto, and the precipitated crystals were collected by filtration, washed with water and dried to obtain crude crystals. The crude crystals were purified by silica gel column chromatography to obtain 490 mg of 7-benzyloxy-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile (compound No. 51) having a melting point of 194° C.

Workup

  1. stirringby stirring at about 50° C. overnight
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water
  6. customdried
  7. customto obtain crude crystals
  8. customThe crude crystals were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08952e88222049258a9d087496e1636e
Source dataset
uspto-grants-2006_06
Patent number
US07067520B2

Reaction notes

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