Potassium Carbonate → 5-(2-Methoxyethyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 593104Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:7]2[CH2:8][NH:9][CH2:10][CH2:11][N:6]2[N:5]=1)([O-:3])=[O:2].BrC1C=C(NC2C=C3CN([CH:31]4[CH2:34][O:33][CH2:32]4)CCN3N=2)C(=O)N(C)C=1.C([O-])([O-])=O.[K+].[K+].BrCCOC>C(#N)C>[CH3:34][O:33][CH2:32][CH2:31][N:9]1[CH2:10][CH2:11][N:6]2[N:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:7]2[CH2:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (190 mg, 1.13 mmol) 125i in acetonitrile (10 mL) was added K2CO3 (311.9 mg, 2.26 mmol) and 1-bromo-2-methoxyethane (188.3 mg, 1.36 mmol). The reaction mixture was heated at 80° C. for 17 h under microwave irradiation. Analysis of reaction mixture by LCMS showed complete conversion to the desired product. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to afford 304a as a white solid (230 mg, 90%), which was used in the next step without further purification. MS-ESI: [M+H]+ 227.0

Workup

customAnalysis of reaction mixture by LCMS

Sources & evidence

ORD record: ord-c8303732f76d4eeea2b6758431c01ba7
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238655B2

Reaction notes

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