Dimethylformamide → HCID 9817635, compound

HRID 1830573Notes

Reaction equation

HRID 1830573 reaction equation
[H-].[Na+].[NH2:3][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]([NH: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 9855798HCID 9855798, compound

Product 1

HCID 9817635HCID 9817635, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 mg of sodium hydride (60%) was added to 500 mg of 7-amino-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile and 8 ml of DMF, followed by stirring at room temperature for about 10 minutes, and then 420 mg of benzyl bromide was added thereto, followed by stirring at about 50° C. for about 2 hours. 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 570 mg of 7-benzylamino-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile (compound No. 2) having a melting point of 165° C.

Workup

  1. stirringby stirring at about 50° C. for about 2 hours
  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-0af2a0b4d8434dc796ed7ac0e6d1ed24
Source dataset
uspto-grants-2006_06
Patent number
US07067520B2

Reaction notes

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