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

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

Reactant 4

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 516892Sodium Bicarbonate

HCID 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.