Dimethylformamide → 1-Benzyl-7-benzylamino-3-formyl-2-methylpyrrolo[2,3-d]pyridazine

HRID 1734522Notes

Reaction equation

HRID 1734522 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10](Br)=[C:9]1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:34]=[O:35]>CCCCCC.O1CCCC1>[CH2:1]([N:8]1[C:12]2=[C:13]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10]([CH:34]=[O:35])=[C:9]1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 194377531-Benzyl-7-benzylamino-3-bromo-2-methylpyrrolo[2,3-d]pyridazineHCID 178418339Butyllithium

Product 1

HCID 194377411-Benzyl-7-benzylamino-3-formyl-2-methylpyrrolo[2,3-d]pyridazineYield 44%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

0.58 g (1.4 mmol) of 1-benzyl-7-benzylamino-3-bromo-2-methylpyrrolo[2,3-d]pyridazine, 3.5 ml (5.7 mmol) of 15% strength solution of n-butyllithium in hexane and 0.55 ml (7 mmol) of dimethylformamide are reacted in 40 ml of anhydrous tetrahydrofuran as described for Example 2a. Yield: 44%, m.p.: 171°-172° C.

Sources & evidence

ORD record
ord-4a13238131dd4614a8536e1e0167e433
Source dataset
uspto-grants-1996_07
Patent number
US05534515

Reaction notes

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