Stannous Chloride → HCID 15958043, compound

HRID 270956Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]3[N:19]([N:27]=[CH:28][C:29]=3[N+:30]([O-])=O)[C:20]=2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[N:17][C:18]3[N:19]([N:27]=[CH:28][C:29]=3[NH2:30])[C:20]=2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 18 mg (0.042 mmol) of 6-(4-benzyloxy-phenyl)-7-cyclohexyl-3-nitro-pyrazolo[1,5-a]pyrimidine in 3 mL of ethyl acetate (EtOAc) was added 40 mg (0.21 mmol) of tin (II) chloride (SnCl2) and the resulting mixture was stirred at 80° C. under argon for 8 h when analysis by TLC indicated only 75% conversion of starting material to product. Therefore, 40 mg (0.21 mmol) of tin (II) chloride (SnCl2) was added, the reaction mixture was heated at 80° C. for 8 h when analysis by TLC indicated complete conversion of starting material to product. The mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, water, brine, dried over sodium sulfate and evaporated to give (after lyophilization) 6 mg (36% yield) of 6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-3-ylamine as a yellow solid as indicated by 1H NMR; LC-MS—calcd for C25H26N4O [M++H]+: 399.21, found: 399.2.

Workup

temperaturethe reaction mixture was heated at 80° C. for 8 h when analysis by TLC
washwashed with saturated sodium bicarbonate solution, water, brine
dry with materialdried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-b3424c69f14c4d3dab99b06b52e135ee
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449488B2

Reaction notes

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