Hydrochloric Acid → 4-(7-(Cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile hydrochloride

HRID 2037013Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.Cl>CCO>[ClH:1].[CH:9]1([NH:8][C:6]2[N:5]3[N:12]=[CH:13][CH:14]=[C:4]3[N:3]=[C:2]([NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[CH:7]=2)[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 23 °C

Procedure

5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine (208 mg, 1 mmol) was suspended in EtOH (1 mL). 4-aminobenzonitrile (236 mg, 2 mmol) and then conc. HCl (125 μL, 1.5 mmol) were added and the reaction was placed in a 95° C. oil bath. After 24 h, additional conc. HCl was added (62 μL). After an additional 24 h, the reaction was cooled to 23° C. and the filter cake was washed with EtOH (2 mL) to afford 4-(7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile hydrochloride (205 mg, 63%) as a light brown solid. LCMS (ES): >90% pure, m/z 291 [M+1]+.

Workup

customwas placed in a 95° C.
waitAfter an additional 24 h
washthe filter cake was washed with EtOH (2 mL)

Sources & evidence

ORD record: ord-8bc8e393a6144021b5e9ee3cdd771c37
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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