Water → ethyl 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate

HRID 869714Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:5]2[N:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:17]=[C:4]2[N:3]=1.[CH2:23]([N:25](CC)[CH2:26][CH3:27])[CH3:24].N1CCCC1.O>CN(C)C(=O)C>[N:25]1([C:2]2[CH:7]=[C:6]([NH:8][CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[N:5]3[N:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:17]=[C:4]3[N:3]=2)[CH2:26][CH2:27][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 5-chloro-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate (5.88 g, 18.1 mmol) in N,N-dimethylacetamide (50 mL) was added triethylamine (5.50 g, 54.3 mmol) and pyrrolidine (1.59 mL, 19.0 mmol) at 0° C. The mixture was heated at 60° C. for 20 h. And then pyrrolidine (1.59 mL, 19.0 mmol) was added and heated at 60° C. for 24 h. After being cooled to ambient temperature, the reaction mixture was poured into water. The resulting precipitate was collected to give ethyl 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate. MS (APCI): m/z 360 (M+H).

Workup

temperatureheated at 60° C. for 24 h
temperatureAfter being cooled to ambient temperature
customThe resulting precipitate was collected

Sources & evidence

ORD record: ord-815f09c574e147b8bcf2a99ad259bfdf
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969376B2

Reaction notes

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