Phosphorus oxychloride → HCID 86599609, compound

HRID 2102404Notes

Reaction equation

HRID 2102404 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:8]([CH3:17])=[N:9][C:10]2[N:11]([N:14]=[CH:15][CH:16]=2)[C:12]=1O>>[Cl:6][C:7]1[C:8]([CH3:17])=[N:9][C:10]2[N:11]([N:14]=[CH:15][CH:16]=2)[C:12]=1[Cl:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432275HCID 178432275, compound

Product 1

HCID 86599609HCID 86599609, compound

Conditions

Temperature
80 °C

Procedure

Phosphorous oxychloride (excess) is added to 6-chloro-5-methylpyrazolo[1,5-a]pyrimidin-7-ol (1.00 equivalent) and heated to 80° C. After 2 hours, the reaction mixture is concentrated under reduced pressure. The resulting residue is poured onto ice and, carefully neutralized with saturated NaHCO3 (pH 8), and diluted with EtOAc. After stirring for 17 hours, the organic layer was separated and the aqueous layer was re-extracted with EtOAc, repeatedly. The combined organic extracts are dried (MgSO4) and concentrated. The product is purified by flash chromatography as necessary.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additionThe resulting residue is poured onto ice
  3. additiondiluted with EtOAc
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was re-extracted with EtOAc
  6. dry with materialThe combined organic extracts are dried (MgSO4)
  7. concentrationconcentrated
  8. customThe product is purified by flash chromatography as necessary

Sources & evidence

ORD record
ord-b1912936c3f542199368e52eb64fa7ce
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

Loading…