N,N-Dimethylaniline → 7-Chloro-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 1830576Notes

Reaction equation

HRID 1830576 reaction equation
O[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([S:11][CH3:12])[C:3]=1[C:13]#[N:14].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([S:11][CH3:12])[C:3]=1[C:13]#[N:14]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178503357HCID 178503357, compound

Product 1

HCID 220480807-Chloro-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile

Procedure

A mixture comprising 2.15 g of 7-hydroxy-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile (compound No. 49), 1.3 g of N,N-dimethylaniline and 5 ml of phosphorus oxychloride was stirred under reflux with heating for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, and poured into ice water, followed by stirring. 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 2.17 g of 7-chloro-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile (compound No. 62) having a melting point of from 201 to 202° C.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for about 3 hours
  3. customAfter the completion of the reaction
  4. stirringby stirring
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customdried
  8. customto obtain crude crystals
  9. customThe crude crystals were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-13b5ac6c7d884db6b383262a7a7cb3cd
Source dataset
uspto-grants-2006_06
Patent number
US07067520B2

Reaction notes

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