Acetic Acid → 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-4,5-dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine
Reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:11]3[CH:12]([CH3:16])[NH:13][CH2:14][CH2:15][N:10]3[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C=O.[BH3-][C:21]#N.[Na+].CC(O)=O>CO>[CH3:7][C:4]1[N:3]([C:8]2[CH:17]=[C:11]3[CH:12]([CH3:16])[N:13]([CH3:21])[CH2:14][CH2:15][N:10]3[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 287g (1.54 g, 1.0 eq., 6.70 mmol), formaldehyde (37% in water) (1.09 g, 2.0 eq., 13.4 mmol), NaBH3CN (2.11 g, 5.0 eq., 33.5 mmol), HOAc (3 mL), and methanol (30 mL). The mixture was stirred at room temperature for 1 h and concentrated under reduced pressure. The residue was partitioned between water (50 mL) and dichloromethane (50 mL). The water phase was extracted with dichloromethane (3×50 mL). The combined organic layer was concentrated under reduced pressure to afford crude 287h, which was used in the next step without further purification. MS-ESI: [M+H]+ 245.0
Workup
- customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
- concentrationconcentrated under reduced pressure
- customThe residue was partitioned between water (50 mL) and dichloromethane (50 mL)
- extractionThe water phase was extracted with dichloromethane (3×50 mL)
- concentrationThe combined organic layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4fb8284486fa43739061959128b2d363
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238655B2
Reaction notes
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