Phosphorus oxychloride → HCID 57743058, compound

HRID 1896419Notes

Reaction equation

HRID 1896419 reaction equation
[F:1][C:2]1[C:3]([CH3:18])=[N:4][C:5]2[N:6]([N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:11]=2)[C:7]=1O.O=P(Cl)(Cl)[Cl:21]>ClCCl>[Cl:21][C:7]1[N:6]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:11]=[C:5]2[N:4]=[C:3]([CH3:18])[C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432076HCID 178432076, compound

Product 1

HCID 57743058HCID 57743058, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-fluoro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-ol x133 (25 mmol, 1 eq, 6.2 g) in POCl3 (150 ml) is heated at 125° C. overnight. After cooling to room temperature, the solution is diluted in dichloromethane and quenched on ice (temperature must be kept under 25° C.). After separation of the organic layer, the aqueous phase is extracted twice with dichloromethane. The cumulated organic layers are dried over MgSO4, filtered, evaporated under reduced pressure and the residue purified by chromatography on silicagel (CH2Cl2) to afford 6.6 g of 7-chloro-6-fluoro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine x136.

Workup

  1. customquenched on ice (temperature must be kept under 25° C.)
  2. customAfter separation of the organic layer
  3. extractionthe aqueous phase is extracted twice with dichloromethane
  4. dry with materialThe cumulated organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customthe residue purified by chromatography on silicagel (CH2Cl2)

Sources & evidence

ORD record
ord-2fb6e3e00e2647d88d9e055f33730721
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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