Potassium Carbonate → HCID 58314678, compound

HRID 624828Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]2[N:3]=1.[C:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH:9]1([NH:8][C:6]2[N:5]3[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]3[N:3]=[C:2]([N:27]3[CH2:26][CH2:25][N:24]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:29][CH2:28]3)[CH:7]=2)[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (500 mg, 2.11 mmol) in dimethylformamide was added 1-Boc-piperazine (1.17 g, 6.33 mmol), potassium carbonate (583 mg, 4.21 mmol) and diisopropyl ethylamine (0.41 mL, 2.5 mmol). The mixture was heated to 80° C. for overnight. Cooled the reaction mixture, added water and filtered the white precipitate to yield tert-butyl 4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate (655 mg, 80% yield). LCMS (M+1=387)

Workup

temperatureCooled the reaction mixture
filtrationfiltered the white precipitate

Sources & evidence

ORD record: ord-12a3de7676234f50b4bc0fd6b83838c3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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