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

HRID 593155Notes

Reaction equation

HRID 593155 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].[N+](C1C=C2CN(C(=O)C)CCN2N=1)([O-])=O.C([O-])([O-])=O.[K+].[K+].Br[CH2:35][CH2:36][O:37][CH3:38]>C(#N)C>[CH3:38][O:37][CH2:36][CH2:35][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

6

Reactant 4

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 580439581-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)ethanoneHCID 580442792-Nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 866839905-(2-Methoxyethyl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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) 209a 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 the 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 327a as a white solid (230 mg, 90%), which was used in the next step without further purification. MS-ESI: [M+H]+ 227.0

Sources & evidence

ORD record
ord-0930cb46372248fb83c57f60ab5415e6
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

Loading…