Hydrazine hydrate (1:1) → 2-(4-(7-Amino-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetohydrazide

HRID 2047078Notes

Reaction equation

C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:34][CH2:33][CH:32]([CH2:35][C:36]([O:38]CC)=O)[CH2:31][CH2:30]2)[C:9]=1Br.O.[NH2:53][NH2:54]>CN(C=O)C>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:30][CH2:31][CH:32]([CH2:35][C:36]([NH:53][NH2:54])=[O:38])[CH2:33][CH2:34]2)[CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 2-5 mL pressure vial was charged ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (0.12 mmol, 95 mg), DMF (1 mL), and hydrazine monohydrate (1 mL). The pressure vial was sealed and heated to 80° C. for 18 hours. After 18 hours, the solvents were removed in vacuo and the product taken on without further purification.

Workup

customThe pressure vial was sealed
customthe solvents were removed in vacuo
customthe product taken on without further purification

Sources & evidence

ORD record: ord-e69eb99a242f4940aeaa3f69178c8109
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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