Ammonia → 5-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047056Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH:11]2[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)[CH:3]=1.[NH3:21]>CO.C(Cl)Cl>[O:18]1[C:14]2([CH2:19][CH2:20][CH:11]([C:4]3[CH:3]=[C:2]([NH2:21])[N:7]4[N:8]=[CH:9][CH:10]=[C:6]4[N:5]=3)[CH2:12][CH2:13]2)[O:15][CH2:16][CH2:17]1

Participants

Conditions

Temperature: 100 °C

Procedure

7-chloro-5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidine (5.58 mmol, 1.64 g) is charged to 10-20 mL microwave vessel. To this vessel is added 10 mL ˜7N NH3 in methanol. The vessel was sealed and heated at 100° C. for 18 hours. After 18 hours, the reaction mixture was cooled to room temperature and diluted with 100 mL DCM. The resulting solution is washed with saturated NaHCO3(aq) and extracted with DCM twice more. The combined organics were dried over Na2SO4 and the solvent removed in vacuo to yield 5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-7-amine (1.52 g, 99% yield) as pale orange solid.

Workup

customThe vessel was sealed
temperaturethe reaction mixture was cooled to room temperature
washThe resulting solution is washed with saturated NaHCO3(aq)
extractionextracted with DCM twice more
dry with materialThe combined organics were dried over Na2SO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-6993870b9d044eaeaabe78dd78843ec2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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