Sodium Hydroxide → 7-Chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidine

HRID 1951284Notes

Reaction equation

HRID 1951284 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:7]3[N:8]=[CH:9][CH:10]=[C:11](O)[N:6]3[N:5]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:16])=O.[OH-].[Na+].C([O-])(O)=O.[Na+]>>[Cl:16][C:11]1[N:6]2[N:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:13]=[C:7]2[N:8]=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178516372HCID 178516372, compound

Product 1

HCID 846651637-Chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidine

Conditions

Temperature
100 °C

Procedure

A mixture of 2-cyclopropylpyrazolo[1,5-a]pyrimidin-7-ol (0.400 g, 2.28 mmol) and phosphorous oxychloride (4.26 ml, 45.7 mmol) in a resealable tube was heated to 100° C. After 4 hrs the solution was cooled to RT and slowly poured onto ice. The mixture was made basic using 2 N NaOH and saturated NaHCO3 and extracted with EtOAc. The combined organic fractions were washed with brine and dried with sodium sulfate. The organic phase solution was passed over a plug of silica gel and concentrated in vacuo to afford 7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidine as a brown oil that was advanced without further purification. MS: Found M+H+=194.1.

Workup

  1. temperatureAfter 4 hrs the solution was cooled to RT
  2. additionslowly poured onto ice
  3. extractionextracted with EtOAc
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5369682248384537b96b7bcde7bb6870
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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